Diisobutylaluminum hydride → HCID 88932536, compound

HRID 1472884Notes

Reaction equation

HRID 1472884 reaction equation
CC(C[AlH]CC(C)C)C.[F:10][C:11]([F:29])([F:28])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24](OC)=[O:25])[N:19]=2)=[CH:14][CH:13]=1>ClCCl>[F:29][C:11]([F:10])([F:28])[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([CH:24]=[O:25])[N:19]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 68312490HCID 68312490, compound

Product 1

HCID 88932536HCID 88932536, compoundYield 21.42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIBAL-H (2.3 mL, 2.300 mmol, 1.0 M in toluene) was slowly added to an orange solution of Example 33A (550 mg, 1.949 mmol) in dichloromethane (10 mL) at −75° C. The reaction was warmed to ambient temperature overnight. Quenched with methanol (10 mL), concentrated to an orange residue, and supported on silica gel. Chromatographed on a Grace Reveleris 12 g column, eluted with 0-60% EtOAc in dichloromethane (25 mL/min) to provide the title compound (135 mg, 0.418 mmol, 21.42% yield) as a beige solid, a mixture of 78% aldehyde and 22% methyl ester by proton NMR. MS (ESI+) m/z 253.1 (M+H).

Workup

  1. customQuenched with methanol (10 mL)
  2. concentrationconcentrated to an orange residue
  3. customChromatographed on a Grace Reveleris 12 g column
  4. washeluted with 0-60% EtOAc in dichloromethane (25 mL/min)

Sources & evidence

ORD record
ord-7a551da8647c4d7f98409090bcd6efd9
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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