Aluminium lithium hydride → HCID 178455369, compound

HRID 1095151Notes

Reaction equation

HRID 1095151 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:14][CH2:13]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C.ClCCl.O=[Mn]=O>[C:22]([Si:19]([CH3:21])([CH3:20])[O:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([O:11][C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=2[CH:3]=[O:2])[CH2:13][CH2:14]1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178498034HCID 178498034, compound

Product 1

HCID 178455369HCID 178455369, compoundYield 44.9%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in example 94c, trans-2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-benzoic acid methyl ester (2.7 g, 6.76 mmol) was reacted with LiAlH4 (1 M, 6.76 mL, 6.76 mmol) in ethyl ether, then oxidized with activated MnO2 (4.64 g, 54 mmol) in dichloromethane to give trans-2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-benzaldehyde as a white solid (Yield 1.12 g, 44%).

Sources & evidence

ORD record
ord-ed6efd7b5ed7491bb9e303b466d2ef77
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

Loading…