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Potassium Carbonate → [8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

HRID 902290
Notes
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Reaction equation

HRID 902290 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16](OS(C(F)(F)F)(=O)=O)[CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>O1CCOCC1.O.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>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[Cl:31])[CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27343222-Chlorophenylboronic acidHCID 86609096(8-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86609095[8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonateYield 89%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (8-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate (0.49 g, 1.05 mmol), 2-chlorophenylboronic acid (0.33 g, 2.1 mmol), potassium carbonate (0.44 g, 3.2 mmol) and lithium chloride (0.13 g, 3.1 mmol) in dioxane (3.75 ml) and water (1.25 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.052 mmol) was added and the reaction mixture heated at 100° C. for 1 hour. The cooled reaction mixture was then partitioned between ethyl acetate (50 mL) and 1 M aqueous sodium hydroxide (50 mL). The organic layer was separated, washed with water (50 mL) dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford an orange oil. Purification by flash chromatography using a solvent gradient of 5 to 10% ethyl acetate in hexane gave 400 mg (89%) of [8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a white solid. HRMS: calcd for C23H21ClO4S+NH4+, 446.11873. found (ESI, [M+NH4]+), 446.1179.

Workup

  1. customwas purged with nitrogen for 20 minutes
  2. customThe cooled reaction mixture
  3. customwas then partitioned between ethyl acetate (50 mL) and 1 M aqueous sodium hydroxide (50 mL)
  4. customThe organic layer was separated
  5. washwashed with water (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford an orange oil
  10. customPurification by flash chromatography

Sources & evidence

ORD record
ord-a3693d14947d4322a9e066a5991d3ff5
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07365095B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes