Tetrahydrofuran → 4-(3-Methoxy-4-nitrophenyl)-3-buten-1-ol

HRID 1451647Notes

Reaction equation

HRID 1451647 reaction equation
ClCCO[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7](C)[CH:6]=1.[Br-].[OH:16][CH2:17]CC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH2:44]1[CH2:48][O:47][CH2:46][CH2:45]1>CCCCCC>[CH3:17][O:16][C:7]1[CH:6]=[C:5]([CH:46]=[CH:45][CH2:44][CH2:48][OH:47])[CH:10]=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11025793Phosphonium, (3-hydroxypropyl)triphenyl-, bromideHCID 199746534-(2-Chloroethoxy)-2-methyl-1-nitrobenzeneHCID 178418339Butyllithium

Product 1

HCID 544595774-(3-Methoxy-4-nitrophenyl)-3-buten-1-ol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The Wittig reaction in THF (100 ml) between 3-methoxy-4-nitrobenzaldehyde (1) (2 g) and 3-hydroxypropyltriphenylphosphonium bromide (2) (5.3 g) in presence of a solution of n-butyllithium (1.6M) in hexane (16.5 ml) gave the title compound (2.6 g) as an oil.

Sources & evidence

ORD record
ord-451678b82fd2420494803018ecd2e808
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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