Potassium Carbonate → FR 110302

HRID 727820Notes

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]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (+)2,2-dibutyl-5-hydroxy-1,2,3,4-tetrahydro-1-naphtol(138mg), 2-chloromethylquinoline(89mg) and potassium carbonate(138mg) in N,N-dimethylformamide(1 ml) was stirred at 70° C. for 3 hours. The cooled mixture was poured into brine(10ml). The separated oil was extracted with brine(5 ml X 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-1-naphtol(162 mg) as white solid.

Workup

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

Sources & evidence

ORD record: ord-0447ffaff54643dfab9930fde501d132
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05045548

Reaction notes

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