Acetic Anhydride → HCID 57087397, compound

HRID 372062Notes

Reaction equation

HRID 372062 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][C:6]([OH:24])([CH3:23])[CH:7]=[CH:8][CH:9]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH3:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1.O>[C:25]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:10]1[CH:9]([CH:8]=[CH:7][C:6]([OH:24])([CH3:23])[CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:13][CH2:12][C:11]1=[O:14])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 54056383HCID 54056383, compound

Product 1

HCID 57087397HCID 57087397, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 7-[2-(5-ethoxy-3-hydroxy-3-methylpent-1-enyl)-5-oxocyclopentyl]heptanol [0.4 g; prepared as hereinbefore described in Example 7(iv)] in dry pyridine (4 ml.) was treated with acetic anhydride (4 ml.) and the resulting solution was allowed to stand at ambient temperature for 3 days and then diluted with water (100 ml.) with external cooling by means of an ice-bath. The resulting aqueous solution was extracted three times with chloroform, and the combined extracts were dried over sodium sulphate. Evaporation in vacuo gave a crude product which was purified by preparative thin layer chromatography on silica gel using a mixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant, to give 2-(7-acetoxyheptyl)-3-(5-ethoxy-3-hydroxy-3-methylpent-1-enyl)cyclopentanone (0.17 g.). Elemental analysis: Found: C, 68.7; H, 10.3%; C22H38O5 requires C, 69.1; H, 10.0%. N.M.R. (approximately 10% w/v solution in deuterochloroform): multiplets at 1.0-1.9δ, 1.9-2.9δ, singlet at 2.05δ, multiplet at 3.35δ, triplet at 4.05δ, (J = 6.5 cycles/second), multiplet at 5.6δ.

Workup

  1. temperaturewith external cooling by means of an ice-bath
  2. extractionThe resulting aqueous solution was extracted three times with chloroform
  3. dry with materialthe combined extracts were dried over sodium sulphate
  4. customEvaporation in vacuo
  5. customgave a crude product which
  6. customwas purified by preparative thin layer chromatography on silica gel using
  7. additiona mixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant

Sources & evidence

ORD record
ord-99bc5e13e1204880a1eae39f8fd1c47f
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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