Acetic Acid → 7-Oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester

HRID 2164579Notes

Reaction equation

HRID 2164579 reaction equation
Cl[C:2]1(Cl)[C:8](=[O:9])[CH:7]2[CH:3]1[CH2:4][CH:5]=[C:6]2[C:10]([O:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(O)(=O)C>O1CCCC1.C(Cl)Cl.[Zn]>[C:14]1([CH:13]([O:12][C:10]([C:6]2[CH:7]3[CH:3]([CH2:4][CH:5]=2)[CH2:2][C:8]3=[O:9])=[O:11])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 134769526,6-Dichloro-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid diphenylmethyl ester

Product 1

HCID 134769537-Oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl esterYield 85.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50 g of 6,6-dichloro-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, from Example 4, in 75 mL of tetrahydrofuran, was added 500 mL of acetic acid and 100 g of zinc dust. This mixture was stirred mechanically for 6 hr at room temperature and then diluted with 1 L of methylene chloride and filtered. The filtrate was evaporated to a residue which was partitioned between methylene chloride and water. The organic layer was washed with brine, dried over sodium sulfate, and evaporated to give a colorless solid which, when triturated with 150 mL of ether-petroleum ether (1:1), afforded 35.1 g (85.5%) of crystalline 7-oxobicyclo[3.2.0]hept-2-ene-2-carboxylic acid diphenylmethyl ester: IR (Nujol mull): 1625, 1715, 1785 cm-1 ; NMR (220 MHz; CDCl3): δ 2.57 (1H, m), 2.89 (3H, m), 3.27 (1H, m), 4.48 (1H, m), 6.80 (1H, s), 6.86 (1H, m) and 7.1-7.4 (10H, m).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to a residue which
  3. customwas partitioned between methylene chloride and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto give a colorless solid which, when
  8. customtriturated with 150 mL of ether-petroleum ether (1:1)

Sources & evidence

ORD record
ord-fcb5fb412ce443f8ba68d1769be7294d
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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