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Sodium Carbonate → 2-[3-(3,4-Dihydro-1-naphthyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole

HRID 1740286
Notes
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Reaction equation

HRID 1740286 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH:8]=1)(=O)=O.[CH3:19][C:20]1([CH3:34])[CH2:24][O:23][C:22]([C:25]2[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=2)=[N:21]1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:7]1([C:27]2[CH:26]=[C:25]([C:22]3[O:23][CH2:24][C:20]([CH3:34])([CH3:19])[N:21]=3)[CH:30]=[CH:29][CH:28]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 10967830Methanesulfonic acid, trifluoro-, 3,4-dihydro-1-naphthalenyl esterHCID 218381293-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)phenyldihydroxyborane

Product 1

HCID 218381802-[3-(3,4-Dihydro-1-naphthyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazoleYield 96.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3,4-dihydro-1-(trifluoromethylsulfonyloxy)naphthalene (1.0 g), 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl-dihydroxyborane (1.1 g), tetrakis(triphenylphosphine)palladium(0) (0.21 g), lithium chloride (0.46 g), 2M sodium carbonate aqueous solution (5.1 ml) in 1,2-dimethoxyethane (12 ml) was heated at 85° C. and stirred vigorously for 3 hours under nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between dichloromethane (35 ml) and 2N sodium carbonate aqueous solution (35 ml) and conc. ammonia solution (2.0 ml). The aqueous layer was extracted again with dichloromethane (35 ml) and the combined organic extracts are dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (30:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-[3-(3,4-dihydro-1-naphthyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (1.05 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between dichloromethane (35 ml) and 2N sodium carbonate aqueous solution (35 ml) and conc. ammonia solution (2.0 ml)
  4. extractionThe aqueous layer was extracted again with dichloromethane (35 ml)
  5. dry with materialthe combined organic extracts are dried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (30:1)
  8. additionThe eluted fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-e79777ee472c43d485b5ae41e270503a
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05968985

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes