Diisobutylaluminum hydride → HCID 67486904, compound

HRID 2103622Notes

Reaction equation

HRID 2103622 reaction equation
C[O:2][C:3](=O)/[C:4](/[C:12]1[CH2:16][C:15]([Br:17])=[CH:14][CH:13]=1)=[CH:5]\[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CC(C[AlH]CC(C)C)C>>[Br:17][C:15]1[CH2:16][C:12](/[C:4](=[CH:5]/[CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)/[CH2:3][OH:2])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67486766HCID 67486766, compound

Product 1

HCID 67486904HCID 67486904, compoundYield 36.3%

Procedure

According to method 16e was used (Z)-2-(4-bromo-cyclopenta-1,3-dienyl)-3-cyclohexyl-acrylic acid methyl ester (116.9 g, max. 0.338 mol), DIBALH (750 ml, 20% in toluene, 0.887 mol) to get 105 g crude product. Purify by silica gel chromatography, eluting with gradient 10:0 to 6:4 hexane:TBME to get 34.7 g pure compound. MS (m/e): 301.0/303.0 (M+H).

Workup

  1. customto get 105 g crude product
  2. customPurify by silica gel chromatography
  3. washeluting with gradient 10:0 to 6:4 hexane

Sources & evidence

ORD record
ord-76fa26569b95481a971e5fc7bce5eddb
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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