HCID 57167084, compound → HCID 57266558, compound

HRID 372063Notes

Reaction equation

HRID 372063 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:17]([CH:18]=[CH:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[CH2:16][CH2:15][C:10]21OCC[O:11]2>Cl>[O:21]=[C:20]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:19]=[CH:18][CH:17]1[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[C:10](=[O:11])[CH2:15][CH2:16]1

Participants

3

Reactant 1

HCID 57167084HCID 57167084, compound

Product 1

HCID 57266558HCID 57266558, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 6-(7-hydroxyheptyl)-7-(3-phenyl-3-oxoprop-1-enyl)-1,4-dioxaspiro[4,4]nonane [1.0 g; prepared as hereinafter described in Example 9(ii)] at dilute hydrochloric acid (2N; 30 ml.) was stirred in 60°-65° C. for 1 hour. The mixture was extracted with diethyl ether and then the combined ethereal extracts were washed with aqueous sodium bicarbonate solution (10% w/v) and then with water, and then dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was purified by preparative thin layer chromatography on silica gel, using a mixture of diethyl ether, n-hexane and ethyl acetate (2:1:1 by volume) as eluant, to give 7-[5-(3-oxo-3-phenylprop-1-enyl)-2-oxocyclopentyl]heptanol (0.16 g.), in the form of a yellow oil. [Elemental analysis: Found: C, 76.9; H, 8.9%; C21H28O5 requires C, 76.8; H, 8.6%, νmax 990 cm-1, 1620 cm-1, 1665 cm-1, 3400 cm-1. N.M.R. (approximately 10% w/v solution in deuterochloroform): triplet at 3.6δ (J = 6 cycles/second), multiplets at 7.85-8.05δ, 7.4-7.65δ, 6.85-7.15δ, 2-2.9δ and 1.1-2.0δ].

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washthe combined ethereal extracts were washed with aqueous sodium bicarbonate solution (10% w/v)
  3. dry with materialwith water, and then dried over anhydrous magnesium sulphate
  4. customThe solution was evaporated
  5. customthe residue was purified by preparative thin layer chromatography on silica gel
  6. additiona mixture of diethyl ether, n-hexane and ethyl acetate (2:1:1 by volume) as eluant

Sources & evidence

ORD record
ord-9ac8552553ce4370824c1ccb9f5e142e
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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