Isopropanol → HCID 54284344, compound

HRID 1995861Notes

Reaction equation

HRID 1995861 reaction equation
[CH3:1][C:2]1([CH3:13])[C@H:4]([CH:5]=[C:6]2[CH2:9][CH2:8][CH2:7]2)[C@H:3]1[C:10](Cl)=[O:11].[CH:14]([OH:17])([CH3:16])[CH3:15]>>[CH3:1][C:2]1([CH3:13])[C@H:4]([CH:5]=[C:6]2[CH2:9][CH2:8][CH2:7]2)[C@H:3]1[C:10]([O:17][CH:14]([CH3:16])[CH3:15])=[O:11]

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 45081796(1R,3R)-3-(Cyclobutylidenemethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride

Product 1

HCID 54284344HCID 54284344, compound

Procedure

A mixture of 12 g of (1R,trans) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylic acid chloride in 25 ml of isopropanol was stirred for 8 hours and was distilled to dryness at 45° C. under reduced pressure. The residue was taken up in isopropyl ether and the solution was washed with water, dried and evaporated to dryness under reduced pressure at 45° C. The residue was chromatographed over silica gel and was eluted with a 9-1 petroleum ether (b.p.=60°-80° C.)-isopropyl ether mixture to recover the fraction with an Rf=0.35. The solvent was evaporated under reduced pressure to obtain 7.8 g of isopropyl (1R,trans) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylate with a boiling point of 64°-66° C. at 0.1 mm Hg and a specific rotation of [α]D20 =-24.5° (c=2% in chloroform).

Workup

  1. distillationwas distilled to dryness at 45° C. under reduced pressure
  2. washthe solution was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure at 45° C
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with a 9-1 petroleum ether (b.p.=60°-80° C.)-isopropyl ether mixture
  7. customto recover the fraction with an Rf=0.35
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-675eaf0f10ff4309acaf10646804f1c3
Source dataset
uspto-grants-1983_09
Patent number
US04406829

Reaction notes

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