HCID 59864416, compound → HCID 69310161, compound

HRID 1093938Notes

Reaction equation

HRID 1093938 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:16]=[C:15]2[C:10]=1[C:11]1[CH2:28][CH2:27][CH2:26][CH2:25][C:12]=1[C:13](=[O:24])[O:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1COCC1>[Si:1]([O:8][C:9]1[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:16]=[C:15]2[C:10]=1[C@H:11]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:12]1[C:13](=[O:24])[O:14]2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 59864416HCID 59864416, compound

Product 1

HCID 69310161HCID 69310161, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 g (74.9 mmol) of 1-tert-butyldimethylsilyloxy-3-pentyl-7,8,9,10-tetrahydro-benzo[c]-chromen-6-one were hydrogenated to completion on palladium/carbon in THF. The catalyst was filtered off, the solvent was removed in vacuo, and the residue was filtered through silica gel with heptane/ethyl acetate (15:1), giving 24.5 g (81%) of (6aR*,10aS*)-1-tert-butyldimethylsilyloxy-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-6-one as a colourless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed in vacuo
  3. filtrationthe residue was filtered through silica gel with heptane/ethyl acetate (15:1)

Sources & evidence

ORD record
ord-81dd871f2ffe41da9129fa65e00a046e
Source dataset
uspto-grants-2012_03
Patent number
US08133887B2

Reaction notes

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