Benzene → HCID 53829222, compound

HRID 1995863Notes

Reaction equation

HRID 1995863 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].C1C=CC=CC=1.[CH3:20][OH:21].N1C=CC=CC=1>O>[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:21][CH3:20])=[O:11]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 887MethanolHCID 1049PyridineHCID 45081793(1R,3S)-3-(Cyclobutylidenemethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride

Product 1

HCID 53829222HCID 53829222, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 30 g of (1R,cis) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylic acid chloride and 50 ml of benzene was added to a solution of 15 g of methanol, 15 g of pyridine and 200 ml of benzene and the mixture was stirred at 20° C. for 8 hours and was then poured into iced water. The decanted organic phase was washed with water, with a sodium bicarbonate solution, with water, with dilute hydrochloric acid and finally with water. The organic phase was dried and evaporated to dryness under reduced pressure at 45° C. The residue was chromatographed over silica gel and was eluted with an 8-2 petroleum ether (b.p.=60°-80° C.)-isopropyl ether mixture to recover the fraction with an Rf=0.5. The solvent was distilled off under reduced pressure at 45° C. and the residue was rectified under reduced pressure to obtain 23 g of methyl (1R,cis) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylate with a boiling point of 63°-64° C. at 0.1 mm Hg and a specific rotation of [α]D20 =+119° (c=1.5% in chloroform).

Workup

  1. washThe decanted organic phase was washed with water, with a sodium bicarbonate solution, with water, with dilute hydrochloric acid and finally with water
  2. customThe organic phase was dried
  3. customevaporated to dryness under reduced pressure at 45° C
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with an 8-2 petroleum ether (b.p.=60°-80° C.)-isopropyl ether mixture
  6. customto recover the fraction with an Rf=0.5
  7. distillationThe solvent was distilled off under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-27bedcea0b3c4551949e84859991f57c
Source dataset
uspto-grants-1983_09
Patent number
US04406829

Reaction notes

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