Lithium diisobutylaluminum hydride → HCID 69666864, compound

HRID 1791054Notes

Reaction equation

HRID 1791054 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Li+].[H-].[Cl:13][CH:14]=[C:15]1[CH:21]=[CH:20][C:19]2[CH:22]=[C:23]([C:26](OC)=[O:27])[CH:24]=[CH:25][C:18]=2[O:17][CH2:16]1>ClCCl>[Cl:13][CH:14]=[C:15]1[CH:21]=[CH:20][C:19]2[CH:22]=[C:23]([CH2:26][OH:27])[CH:24]=[CH:25][C:18]=2[O:17][CH2:16]1

Participants

4

Reactant 2

HCID 22042274Lithium diisobutylaluminum hydrideHCID 69667024HCID 69667024, compound

Product 1

HCID 69666864HCID 69666864, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.72 ml (2.72 mmol) of a lithium diisobutylaluminum hydride solution are added at a temperature of −78° C. to 217 mg (0.87 mmol) of methyl 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 32, in solution in 10 ml of dichloromethane. The solution is stirred at this temperature for 1 hour. A conventional treatment makes it possible to isolate 211 mg (100%) of [3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]methanol in the form of a white solid comprising two Z/E isomers as a mixture in a 90/10 ratio; 1H NMR (C6D6): 6.98 (d, J=8.2 Hz, 1H), 6.97 (m, 1H), 6.90 (dd, J=8.2 Hz and 2.2 Hz, 1H), 6.07 (d, J=11.8 Hz, 1H), 5.86 (d, J=11.8 Hz, 1H), 5.74 (s, 1H), 4.68 (s, 2H), 4.28 (4.1) (s, 2H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-aafb996dd83d4cf1a59f6366ed0cb2bc
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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