Anisole → 3-Phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic Acid

HRID 2164584Notes

Reaction equation

HRID 2164584 reaction equation
[C:1]1([S:7][C:8]2[CH2:14][CH:13]3[CH:10]([C:11](=[O:15])[CH2:12]3)[C:9]=2[C:16]([O:18]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[C:1]1([S:7][C:8]2[CH2:14][CH:13]3[CH:10]([C:11](=[O:15])[CH2:12]3)[C:9]=2[C:16]([OH:18])=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 134769553-Phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic Acid, Diphenylmethyl Ester

Product 1

HCID 134769593-Phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic AcidYield 84.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 150 mg of 3-phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, and 135 mg of anisole in 3 mL of trifluoroacetic acid was stirred at room temperature for 15 min. The solvent was removed with a stream of nitrogen leaving a residual oil which when triturated with ether afforded 77 mg (84%) of colorless crystals of 3-phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid. NMR (220 MHz; CDCl3): δ 2.27 (1H, dd, J=17, 3), 2.75 (1H, m), 2.68 (1H, m), 3.0-3.25 (1H, m), 4.50 (1H, m), 7.2-7.4 (3H, m), and 7.4-7.6 (2H, m).

Workup

  1. customThe solvent was removed with a stream of nitrogen leaving a residual oil which when
  2. customtriturated with ether

Sources & evidence

ORD record
ord-b046c95ea2f544e6ac95c273c2af1ab1
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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