Anisole → 3-Phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid

HRID 2164590Notes

Reaction equation

HRID 2164590 reaction equation
C1(C([O:14][C:15]([C:17]2[CH:18]3[CH:21]([CH2:22][C:23]=2[S:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]([CH:31]([OH:33])[CH3:32])[C:19]3=[O:34])=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[C:25]1([S:24][C:23]2[CH2:22][CH:21]3[CH:18]([C:19](=[O:34])[CH:20]3[CH:31]([OH:33])[CH3:32])[C:17]=2[C:15]([OH:16])=[O:14])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 134769653-Phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid diphenylmethyl ester

Product 1

HCID 204047913-Phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acidYield 80.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 50 mg of 3-phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid diphenylmethyl ester, and 50 mg of anisole in 1 mL of trifluoroacetic acid was stirred for 5 min at room temperature after which time the solvent was removed by evaporation. Trituration of the residue with ether-petroleum ether afforded 26 mg (80%) of 3-phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid as colorless crystals. IR (Nujol mull): 1765, 1650, 1535 cm-1 ; NMR (220 MHz; CDCl3 /DMSO-D6): δ 1.18 (3H, d, J=6.5), 2.32 (1H, dd, J=19, 3.5), 2.67 (1H, m), 2.85 (1H, dd, J=19, 8), 3.07 (1H, m), 3.92 (1H, dq, J=6.5, 6.5), 4.41 (1H, m), and 7.3-7.6 (5H, m).

Workup

  1. customwas removed by evaporation

Sources & evidence

ORD record
ord-cc4c5153994e4e6aaff6a197eb06ea13
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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