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Potassium Carbonate → FR 110302

HRID 1089242
Notes
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Reaction equation

HRID 1089242 reaction equation
[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[CH:6]1[OH:16])[CH2:2][CH2:3][CH3:4].Cl[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)[CH:6]1[OH:16])[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 105166192,2-Dibutyl-5-hydroxy-1,2,3,4-tetrahydro-1-naphthol

Product 1

HCID 164102FR 110302Yield 77.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 57417360
Sodium chloride; water
Solvent

Conditions

Temperature
70 °C

Procedure

A mixture of (+)-2,2-dibutyl-5-hydroxy-1,2,3,4-tetrahydro-1-naphtol(138mg), 2-chloromethylquinoline(89 mg) and potassium carbonate(138 mg) in N,N-dimethylformamide(1 ml) was stirred at 70° C. for 3 hours. The cooled mixture was poured into brine(10 ml). The separated oil was extracted with brine(5 ml×3). The combined organic layers were washed with brine(5 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by columnchromatography on silica gel(elution by 15% ethyl acetate in hexane) to give a pale yellow syrup. The residual syrup was crystallized from methanol to yield (+)-2,2-dibutyl-5-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1naphtol(162 mg) as white solid.

Workup

  1. extractionThe separated oil was extracted with brine(5 ml×3)
  2. washThe combined organic layers were washed with brine(5 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by columnchromatography on silica gel(elution by 15% ethyl acetate in hexane)
  6. customto give a pale yellow syrup
  7. customThe residual syrup was crystallized from methanol

Sources & evidence

ORD record
ord-b6e24b56b23f4244b272a4042e246323
Source dataset
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04965274

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes