Diisobutylaluminum hydride → HCID 21959265, compound

HRID 2055053Notes

Reaction equation

HRID 2055053 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[C:22]2[C:21]3[CH:20]=[CH:19][C:18]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[CH:17][C:16]=3[O:15][CH2:14][C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])=[CH:8][C:7]=2[O:6]1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:27]([Si:24]([CH3:26])([CH3:25])[O:23][C:18]1[CH:19]=[CH:20][C:21]2[C:22]3[CH:5]([CH2:4][CH:3]=[O:2])[O:6][C:7]4[CH:8]=[C:9]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34])[CH:10]=[CH:11][C:12]=4[C:13]=3[CH2:14][O:15][C:16]=2[CH:17]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 21051987HCID 21051987, compound

Product 1

HCID 21959265HCID 21959265, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., to a solution of [2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-acetic acid methyl ester, the compound prepared as in Example 96 (120 mg, 0.21 mmol) in toluene (2 mL) was added DIBAL (0.28 mL, 1.5 M in toluene, 2 eq.) at −78° C. and stirred for 6 hours at −78° C. The reaction mixture was then quenched at −78° C. with chilled MeOH. HPLC purification of the residue yielded the title compound as a thick oil.

Workup

  1. customAt −78° C.
  2. customThe reaction mixture was then quenched at −78° C. with chilled MeOH
  3. customHPLC purification of the residue

Sources & evidence

ORD record
ord-d3e45d7f07e9453ca932344bc46a0d06
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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