Sodium methanethiolate → 1-(2-Hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol

HRID 892510Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[C:11]([CH3:13])C.[CH3:22][S-].[Na+]>CN(C)C=O>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[CH:11][CH2:13][CH3:22]

Participants

Conditions

Temperature: 120 °C

Procedure

7.13 g of 1-(2-methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol were dissolved in 100 ml of dimethylformamide at room temperature and 5.29 g of sodium methanethiolate were added. After stirring at 120° C. for 2 hours the mixture was allowed to cool to room temperature and then evaporated. Water and ethyl acetate were added, and the organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 4.53 g of 1-(2-hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol in the form of an oil.

Workup

temperatureto cool to room temperature
customevaporated
additionWater and ethyl acetate were added
customthe organic phase was separated
dry with materialdried over sodium sulphate
customevaporated
customThe residue was chromatographed on silica gel
washfor the elution

Sources & evidence

ORD record: ord-261495a6734b439388bd3208fcfde01b
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05118694

Reaction notes

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