Methyl Bromide → 2-(3-(Benzyloxy)phenyl)-2-methylpropanal

HRID 2242585Notes

Reaction equation

HRID 2242585 reaction equation
C([O:8]C1C=C(CC#N)C=CC=1)C1C=CC=CC=1.[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([C:32]([CH3:36])([CH3:35])[C:33]#N)[CH:29]=[CH:30][CH:31]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CBr.CC(C[AlH]CC(C)C)C>[OH-].[Na+].CS(C)=O>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([C:32]([CH3:36])([CH3:35])[CH:33]=[O:8])[CH:29]=[CH:30][CH:31]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6323Methyl BromideHCID 14487Diisobutylaluminum hydrideHCID 5198313-BenzyloxyphenylacetonitrileHCID 204968632-(3-(Benzyloxy)phenyl)-2-methylpropanenitrile

Product 1

HCID 198553592-(3-(Benzyloxy)phenyl)-2-methylpropanal

Reagents, catalysts & solvents 1

HCID 86587531NaOH DMSOSolvent

Procedure

Commercially available (3-benzyloxy-phenyl)-acetonitrile (I) was converted to 2-(3-benzyloxy-phenyl)-2-methyl-propionitrile (II) using methyl bromide gas in NaOH/DMSO, followed by a reduction with DIBAL-H yielding 2-(3-benzyloxy-phenyl)-2-methylpropionaldehyde (III). Further reduction of III with NaBH4 afforded 2-(3-benzyloxy-phenyl)-2-methyl-propan-1-ol (IV). Wittig reactions of III with pentyltriphenylphosphonium bromide, trimethyl-4-phosphonocrotonate and trimethyl phosphonoacetate, produced 1-(1,1-dimethyl-hept-2-enyl)-3-phenethyl-benzene (V), 6-(3-benzyloxy-phenyl)-6-methyl-hepta-2,4-dienoic acid methyl ester (VIa), and 4-(3-benzyloxy-phenyl)-4-methyl-pent-2-enoic acid methyl ester (VIb) respectively (Scheme 1).

Sources & evidence

ORD record
ord-a4d0e0c2f63a4aefb5b483acdde33971
Source dataset
uspto-grants-2010_03
Patent number
US07671052B2

Reaction notes

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