5-(Benzyloxy)-2-nitrobenzaldehyde → 1-[5-(Benzyloxy)-2-nitrophenyl]-2-buten-1-ol

HRID 396125

Reaction equation

HRID 396125 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]([Mg]Br)=[CH:21][CH3:22]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([CH:14]([OH:15])[CH:20]=[CH:21][CH3:22])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 38498355-(Benzyloxy)-2-nitrobenzaldehydeHCID 178456053HCID 178456053, compound

Product 1

HCID 700006001-[5-(Benzyloxy)-2-nitrophenyl]-2-buten-1-olYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Analogously to the procedure of example II, starting from 3.00 g (11.66 mmol) of 5-benzyloxy-2-nitrobenzaldehyde in 60 ml of THF and 37.8 ml (18.66 mmol) of a 0.5 M 1-propenylmagnesium bromide solution in THF at −78° C., 1.95 g (56%) of 1-[5-(benzyloxy)-2-nitrophenyl]-2-buten-1-ol are obtained as an E/Z mixture.

Sources & evidence

ORD record
ord-fc127e8d8a3042f9b4bb130d9f7a5698
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Linked notes

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