Acetic Acid → HCID 54513106, compound

HRID 986322Notes

Reaction equation

HRID 986322 reaction equation
[Cl:1][C:2]1[C:3](=[O:30])[C:4](=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([O:7][Si](C)(C)C)[CH:6]=1.C(O)(=O)C.O1CCCC1.C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[C:3](=[O:30])[C:4](=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:5]([OH:7])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 53782227HCID 53782227, compound

Product 1

HCID 54513106HCID 54513106, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

31 g of the mixture of E- and Z-isomes of 2-chloro-5-(6-methoxycarbonylhexylidene)-4-octyl-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 2 was mixed with 3 ml of a 6:1:3 mixture of acetic acid, tetrahydrofuran and water, and the mixture was stirred for 2 hours. A saturated aqueous solution of sodium bicarbonate was added, and the mixture was extracted with ether. The extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on a silica gel column to give 25 mg (yield 97%) of a mixture of Z- and E-isomers of 2-chloro-4-hydroxy-5-(6-methoxxycarbonylhexylidene-4-octyl-2-cyclopentenone.

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-706d43b00b034d42bb712f1e7960bfed
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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