Acetone → HCID 70631647, compound

HRID 1282884Notes

Reaction equation

[OH:1][CH:2]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH:6]1[CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:15]([OH:17])=[O:16].CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.CO>[O:1]=[C:2]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH:6]1[CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:15]([OH:17])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.75 g. of 7-(3-hydroxy-1-octenyl)-1,4-dioxaspiro[4.4]non-6-ylheptanoic acid in 40 ml. of acetone was cooled to 0°C. and treated with 2.0 ml. of Jones Reagent. After stirring for 10 minutes, at 0°C., the reaction mixture was treated with 5 ml. of methanol, dilute sodium bicarbonate until basic and water. Following acidification with acetic acid, the mixture was extracted with ether and the extract washed with water, dried and evaporated. Silica chromatography of the resulting residue with 30% ethyl acetate-hexane gave 0.355 g. of the title product, λmaxfilm 3.1 (shoulder), 5.8, 6.1, 6.75, 8.6, 9.6, 10.1, 10.5 μ. NMR: δ 6.78 (dd, 1, J=8.3, 15.8, 13-H), 6.18 (d, 1, J- 15.8, 14-H), 3.92 (S, 4, ketal) ppm. UV: λmaxEtOH 230 mμ (ε 10,000). Mass spectrum M+ at m/e 380.2523 (theory 380.2562).

Workup

additiontreated with 2.0 ml
additionthe reaction mixture was treated with 5 ml
extractionthe mixture was extracted with ether
washthe extract washed with water
customdried
customevaporated
customSilica chromatography of the resulting residue with 30% ethyl acetate-hexane gave 0.355 g

Sources & evidence

ORD record: ord-f87b4d7251ad470bbdad242a151fdd95
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03972917

Reaction notes

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