Hydrochloric Acid → HCID 56638015, compound

HRID 637326Notes

Reaction equation

HRID 637326 reaction equation
[CH3:1][C:2]1([CH3:22])[CH:4]([CH:5]=[C:6]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:3]1[C:19]([O-:21])=[O:20].CO.Cl>O>[CH3:1][C:2]1([CH3:22])[CH:4]([CH:5]=[C:6]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[CH:3]1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131714448HCID 131714448, compound

Product 1

HCID 56638015HCID 56638015, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 590 mg Sof the product of Step B, 20 ml of methanol, 10 ml of acetane and 20 ml of aqueous N hydrochloric acid was stirred at 20° C. for 6 hours and was poured into water. The mixture was extracted with methylene chloride and the organic phase was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 4-6 hexane-ethyl acetate mixture to obtain 364 mg of (1R,transΔZ) 2,2-dimethyl-3-[2-tert.-butoxy-2-tert.-butoxycarbonyl-ethenyl]-cyclopropane-carboxylic acid melting at 85° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. customthe organic phase was evaporated to dryness under reduced pressure
  3. customThe residue was chromatographed over silica gel
  4. washwas eluted with a 4-6 hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-d570373bd2dd47988144812a304c049f
Source dataset
uspto-grants-1985_12
Patent number
US04556666

Reaction notes

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