HCID 86597289, compound → HCID 86597291, compound

HRID 2223336Notes

Reaction equation

HRID 2223336 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH2:31][C@@:29]2([CH3:30])[C@@H:25]([CH2:26][CH2:27][C@@H:28]2[O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C@@:24]2([CH:40]=[O:41])[C:15]=1[C:16]1[CH:17]=[CH:18][C:19]([O:42][CH3:43])=[CH:20][C:21]=1[CH2:22][CH2:23]2)C1C=CC=CC=1>O1CCCC1.CO.[Pd]>[Si:33]([O:32][C@H:28]1[CH2:27][CH2:26][C@H:25]2[C@@:24]3([CH:40]=[O:41])[C@H:15]([C@@H:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH2:31][C@:29]12[CH3:30])[C:16]1[CH:17]=[CH:18][C:19]([O:42][CH3:43])=[CH:20][C:21]=1[CH2:22][CH2:23]3)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

4

Reactant 1

HCID 86597289HCID 86597289, compound

Product 1

HCID 86597291HCID 86597291, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 14.36 g of tetraene 6 in 400 ml of tetrahydrofuran/methanol (3:1) is mixed with 2.8 g of palladium (10% on carbon) and stirred under a hydrogen atmosphere (100 bar) for two days at room temperature. This reaction is repeated twice. For working-up, it is filtered on Celite and concentrated by evaporation in a vacuum. The residue is purified by column chromatography (cyclohexane/ethyl acetate) and yields 8.25 g of 7 as a colorless foam (GC-MS: m/z theor.: 514, pract.: 514).

Workup

  1. filtrationit is filtered on Celite
  2. concentrationconcentrated by evaporation in a vacuum
  3. customThe residue is purified by column chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-80424c1520d54c21be4f098d99a4de21
Source dataset
uspto-grants-2008_05
Patent number
US07375098B2

Reaction notes

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