Acetone → 7-[5-(3-Hydroxy-3-methyl-4-propoxybut-1-enyl)2-oxocyclopentyl] heptanoic acid

HRID 259205Notes

Reaction equation

HRID 259205 reaction equation
[OH:1][C:2]([CH3:28])([CH2:23][O:24][CH2:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].CC(C)=O.O.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[OH:1][C:2]([CH3:28])([CH2:23][O:24][CH2:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:7](=[O:8])[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 540128087-{7-(3-Hydroxy-3-methyl-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]non-6-yl}heptanoic acidHCID 86626551p-Toluenesulfonic acid dihydrate

Product 1

HCID 542381327-[5-(3-Hydroxy-3-methyl-4-propoxybut-1-enyl)2-oxocyclopentyl] heptanoic acidYield 9.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Crude 7-{7-(3-hydroxy-3-methyl-4 -propoxybut-1-enyl)-1,4-dioxaspiro[4,4]non-6-yl}heptanoic acid [1.04 g.; prepared as hereinbefore described in Example 1 (viii)], undried acetone (50 ml.) containing a small amount of water and p-toluenesulphonic acid dihydrate (0.1 g.) were left to stand together at room temperature for 24 hours. The mixture was then added to excess diethyl ether and washed with water until the washings were neutral. The ether solution was dried over sodium sulphate and evaporated, to give crude 7-[5-(3-hydroxy-3-methyl-4-propoxybut-1-enyl)-2-oxocyclopentyl] heptanoic acid (0.83 g.). This material 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 7-[5-(3-hydroxy-3-methyl-4-propoxybut-1-enyl)2-oxocyclopentyl] heptanoic acid (90 mg.). Elemental analysis: found C, 67.3; H, 9.9%; C20H34O5 requires C, 67.7; H, 9.7%.

Workup

  1. waitwere left
  2. washwashed with water until the washings
  3. dry with materialThe ether solution was dried over sodium sulphate
  4. customevaporated
  5. customto give crude 7-[5-(3-hydroxy-3-methyl-4-propoxybut-1-enyl)-2-oxocyclopentyl] heptanoic acid (0.83 g.)
  6. customThis material was purified by preparative thin layer chromatography on silica gel
  7. additiona mixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant

Sources & evidence

ORD record
ord-c89d08bcc0b4414c8af2033a5ff98fb2
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Reaction notes

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