Potassium tert-butoxide → HCID 13767613, compound

HRID 1981964Notes

Reaction equation

HRID 1981964 reaction equation
Br[CH:2]([CH2:17][OH:18])[CH2:3][CH:4]([CH:6]1[C:14]2([CH3:15])[CH:9]([CH:10]([OH:16])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)[CH3:5].CC(C)([O-])C.[K+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C>[CH3:15][C:14]12[CH2:13][CH2:12][CH2:11][CH:10]([OH:16])[CH:9]1[CH2:8][CH2:7][CH:6]2[CH:4]([CH3:5])[CH2:3][CH:2]1[CH2:17][O:18]1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 23672064Monosodium phosphateHCID 86740842HCID 86740842, compound

Product 1

HCID 13767613HCID 13767613, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 4.6 g of [3aS-[3a alpha, 3(R*,R*), 7beta, 7a beta]]-3-(3-Bromo-4-hydroxy-1-methylbutyl)hexahydro-3a-methyl-1H-inden-7-ol in 145 mL of dry t-butanol under an argon atmosphere and at room temperature is added 2.1 g of potassium t-butoxide. After stirring 50 minutes the mixture was cooled in an ice bath and 10 mL of saturated aqueous sodium dihydrogen phosphate was added. The mixture was stirred 10 minutes then poured into 500 mL of ice water and extracted 3×200 mL of methylene chloride. The combined extracts were washed successively with water, brine then dried over anhydrous sodium sulfate. Filtration and evaporation of solvent in vacuo gave 3.5 g of crude product. Medium pressure liquid chromatography eluting with hexane/ethyl acetate (1:1) gave 2.9 g (84%) of [3aS[3a alpha,3(R*,S*),7beta, 7a beta]]-Hexahydro-3a-methyl-3-(1-methyl-2-oxiranylethyl)- 1H-inden-7-ol. The analytical sample was crystallized from hexane/ethyl acetate. MP 62.5°-63° C.; [α]D25 -31.26° (c 1.0300, CHCl3). Calculated for C15H24O2 : C, 76.23; H, 10.24. Found: C 75.95; H, 10.01.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringThe mixture was stirred 10 minutes
  3. extractionextracted 3×200 mL of methylene chloride
  4. washThe combined extracts were washed successively with water, brine
  5. dry with materialthen dried over anhydrous sodium sulfate
  6. filtrationFiltration and evaporation of solvent in vacuo
  7. customgave 3.5 g of crude product
  8. washMedium pressure liquid chromatography eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-f8c230be3a2e4eebbe95358944bc2e39
Source dataset
uspto-grants-1986_06
Patent number
US04594432

Reaction notes

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