Chloroform → HCID 53257409, compound

HRID 2406851Notes

Reaction equation

HRID 2406851 reaction equation
C(Cl)(Cl)Cl.[CH3:5][C:6]1[CH:7]([OH:16])[CH:8]([OH:15])[CH:9]([C:12]([CH3:14])=[CH2:13])[CH2:10][CH:11]=1>C(Cl)Cl>[CH3:5][C:6]1[C@@H:7]([OH:16])[C@H:8]([OH:15])[C@H:9]([C:12]([CH3:14])=[CH2:13])[CH2:10][CH:11]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 533453613-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

Product 1

HCID 53257409HCID 53257409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 945 mg epoxide (−)-cis-verbenole (1R,2R,4S,5R,6S)-2 ([α]D25=−85.6 (c0.82, CHCl3)) in 12 ml methylene chloride was added, stiffing continuously, into a suspension of 2 g K10 (Fluka) clay (calcinated for 3 hours under 110° C.) in 15 ml of methylene chloride. The reaction mixture was stirred for 1 hour under room temperature. The catalyst was filtered, rinsed by ethyl acetate, the solvent was evaporated. The residue was separated by column chromatography using SiO2 (60-200μ; Merck), a solution of diethyl ether in hexane 5 to 100% was used as an eluent. 270 mg (29%) of (1R,2R,6s)-1a (ee 94%, ([α]D27=−84.0 (c 3.47, CHCl3)) was obtained as a result. Enantiomeric purity of the compound 1a was evaluated by the data of gas-liquid chromatography with mass spectroscopy in chiral column.

Workup

  1. additionstiffing continuously, into a suspension of 2 g
  2. filtrationThe catalyst was filtered
  3. washrinsed by ethyl acetate
  4. customthe solvent was evaporated
  5. customThe residue was separated by column chromatography
  6. custom270 mg (29%) of (1R,2R,6s)-1a (ee 94%, ([α]D27=−84.0 (c 3.47, CHCl3)) was obtained as a result

Sources & evidence

ORD record
ord-fa1c41cf7a8b4f50aac028fb8097eeef
Source dataset
uspto-grants-2014_08
Patent number
US08809391B2

Reaction notes

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