Acetic Acid → HCID 56612422, compound

HRID 35490Notes

Reaction equation

HRID 35490 reaction equation
[Si]([O:8][CH:9]([CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[CH:10]=[CH:11][CH:12]1[CH:16]([CH:17]([OH:27])[C:18]#[C:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15](=[O:28])[CH:14]=[CH:13]1)(C(C)(C)C)(C)C.C(O)(=O)C.O1CCCC1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[OH:8][CH:9]([CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1)[CH:10]=[CH:11][CH:12]1[CH:16]([CH:17]([OH:27])[C:18]#[C:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15](=[O:28])[CH:14]=[CH:13]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 56638654HCID 56638654, compound

Product 1

HCID 56612422HCID 56612422, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

63 mg (0.133 mmole) of 4-(3-t-butyldimethylsilyloxy-3-cyclopentyl-1-propenyl)-5-(1-hydroxy-6-methoxycarbonyl-2-hexyn-1-yl)-2-cyclopentenone obtained in Example 25 was dissolved in 2 ml of a mixed solvent composed of acetic acid, tetrahydrofuran and water in a ratio of 3:2:2, and the solution was stirred for 20 hours. An aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixture to perform extraction. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel 5 g; eluent, hexane:ethyl acetate=5:1→1:1) to give 38 mg (yield 79%) of 4-(3-hydroxy-3-cyclopentyl-1-propenyl)-5-(1-hydroxy-6-methoxycarbonyl-2-hexyn-yl)-2-cyclopentenone. The resulting compound had the following spectral data.

Workup

  1. extractionextraction
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe dried product was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-47c58977230c4fd7967d76880a7aea2c
Source dataset
uspto-grants-1988_08
Patent number
US04766147

Reaction notes

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