Ethyl Acetate → HCID 13767616, compound

HRID 1981965Notes

Reaction equation

HRID 1981965 reaction equation
[CH3:1][C:2]12[CH:10]([CH:11]([CH3:16])[CH2:12][CH:13]3[CH2:15][O:14]3)[CH2:9][CH2:8][CH:7]1[CH:6]([OH:17])[CH2:5][CH2:4][CH2:3]2.C(OCC)(=O)C.[CH3:24][Si:25](C1NC=CN=1)([CH3:27])[CH3:26]>O>[CH3:24][Si:25]([O:17][CH:6]1[CH2:5][CH2:4][CH2:3][C:2]2([CH3:1])[CH:7]1[CH2:8][CH2:9][CH:10]2[CH:11]([CH3:16])[CH2:12][CH:13]1[CH2:15][O:14]1)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 13767613HCID 13767613, compoundHCID 14420972TMS-Imidazole

Product 1

HCID 13767616HCID 13767616, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.4 g of [1R-[1alpha(R*,S*), 3a beta, 4beta, 7a alpha]]-Octahydro-7a-methyl-1-(1-methyl-2-oxiranylethyl)-1H-inden-4-ol and 40 mL of ethyl acetate is added 1.64 g of trimethylsilylimidazole. The mixture was stirred under a dry argon atmosphere at room temperature for 20 minutes then poured into 100 mL of cold water and extracted 3×25 mL of heptane/ethyl acetate (1:1). The extracts were washed with 3×50 Ml of water and dried over anhydrous sodium sulfate. The mixture was filtered and solvent removed in vacuo. Chromatography on silica gel (2.5×100 cm Altex column, 40-60μ silica gel) eluting with hexane/ethyl acetate (6:1) gave 1.81 g (99%) of [1R-[1alpha(R*,S*),3a beta, 4beta, 7a alpha]]-Octahydro-7a-methyl-1-(1-methyl-2-oxiranylethyl)-1H-inden-4-ol trimethylsilyl ether. This material which contained traces of starting material and slowly reverted to starting material on standing was used with no further purification.

Workup

  1. extractionextracted 3×25 mL of heptane/ethyl acetate (1:1)
  2. washThe extracts were washed with 3×50 Ml of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe mixture was filtered
  5. customsolvent removed in vacuo
  6. washChromatography on silica gel (2.5×100 cm Altex column, 40-60μ silica gel) eluting with hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-c4db898e0fb148eb81c2c18b2bc3429c
Source dataset
uspto-grants-1986_06
Patent number
US04594432

Reaction notes

Loading…