HCID 23286133, compound → HCID 23286156, compound

HRID 1637380Notes

Reaction equation

HRID 1637380 reaction equation
[OH:1][CH2:2][C:3]#[C:4][CH2:5][O:6][CH2:7][C:8]12[CH:19]3[CH2:20][C:15]([CH:27]=[O:28])([C:16]1([C:24]([O-:26])=[O:25])[C:17]([CH:21]([CH3:23])[CH3:22])=[CH:18]3)[CH:14]1[CH:10]([CH:11]([CH3:29])[CH2:12][CH2:13]1)[CH2:9]2.[H][H]>CO.[OH-].[OH-].[Pd+2]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][C:8]12[CH:19]3[CH2:20][C:15]([CH:27]=[O:28])([C:16]1([C:24]([OH:26])=[O:25])[C:17]([CH:21]([CH3:22])[CH3:23])=[CH:18]3)[CH:14]1[CH:10]([CH:11]([CH3:29])[CH2:12][CH2:13]1)[CH2:9]2

Participants

5

Reactant 2

HCID 23286133HCID 23286133, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23286156HCID 23286156, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The alcohol obtained above was dissolved in methanol and palladium hydroxide on carbon (Pearlman's catalyst) was added. The reaction mixture was stirred under one atmosphere of hydrogen for 3 hours. The mixture was filtered and the filtrate was concentrated in vacuo to give the title compound. 1H NMR (CDCl3): δ0.82 (3H, d, J=6.9), 0.95 (3H, d, J=6.7), 1.02 (3H, d, J=6.8), 1.20-2.10 (15H, m), 2.33 (1H, m), 2.37 (1H, m), 3.26-4.00 (6H, m), 6.02 (1H, m), 9.88 (1H, s).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-94fdbb5033d4408d878007e075f1f8d4
Source dataset
uspto-grants-2000_03
Patent number
US06040463

Reaction notes

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