Acetic Acid → 3-Phenylthio-7-oxobicyclo[3.2.0]heptan-2-carboxylic acid, diphenylmethyl ester

HRID 2164580Notes

Reaction equation

HRID 2164580 reaction equation
[O:1]=[C:2]1[CH:8]2[CH:4]([CH2:5][CH:6]=[C:7]2[C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.C(N(CC)CC)C.[C:32]1([SH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(O)(=O)C>C1COCC1>[C:32]1([S:38][CH:6]2[CH2:5][CH:4]3[CH:8]([C:2](=[O:1])[CH2:3]3)[CH:7]2[C:9]([O:11][CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7969ThiophenolHCID 8471TriethylamineHCID 134769537-Oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester

Product 1

HCID 134769543-Phenylthio-7-oxobicyclo[3.2.0]heptan-2-carboxylic acid, diphenylmethyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Twenty grams of 7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, 13, were dissolved in 40 mL of THF by gentle warming. To this solution at room temperature was added 1.0 mL of triethylamine and 13.0 mL of thiophenol. The resulting solution was stirred under argon at room temperature for 1 hr, after which time 0.5 mL of acetic acid was added, and the solvent was removed by rotary evaporation at 40°. Crystallization from ether at room temperature afforded 21 g (78%) (total of 2 crops) of 3-phenylthio-7-oxobicyclo[3.2.0]heptan-2-carboxylic acid, diphenylmethyl ester, 14. NMR (220 MHz; CDCl3): δ 2.23 (1H, m), 2.43 (1H, m), 2.84 (1H, m), 3.07 (2H, m), 3.41 (1H, m), 3.80 (2H, m), 6.77 (1H, s), and 7.0-7.3 (15H, m).

Workup

  1. customthe solvent was removed by rotary evaporation at 40°
  2. customCrystallization from ether at room temperature

Sources & evidence

ORD record
ord-4750bbb76ab34e35abe03a553a340007
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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