4-Fluorobenzaldehyde → 4-(4-Fluorophenyl)but-3-en-1-ol

Temperature

0 °C

n-Butyllithium (1.6M in H, 100 ml) was added dropwise to a stirred suspension of (3-hydroxypropyl)triphenylphosphonium bromide (32.1 g) in dry THF (200 ml) cooled to 0° C. under nitrogen. A solution of 4-fluorobenzaldehyde (9.93 g) in dry THF (100 ml) was added dropwise and the mixture stirred under nitrogen at 0° C. for 30 min and at room temperature for a further 1.5 h. The mixture was carefully diluted with water (25 ml), the solvent evaporated in vacuo at 40° and the residue partitioned between EA (200 ml) and water (200 ml). The aqueous phase was re-extracted with EA (200 ml), the organic phases combined, dried and evaporated in vacuo to give a brown oil. Purification by FCC eluting with CX-ER (1:1) gave the title compound as a colourless oil (6.33 g). T.l.c. (CX-ER 1:1) Rf 0.13

1. customthe solvent evaporated in vacuo at 40°
2. customthe residue partitioned between EA (200 ml) and water (200 ml)
3. extractionThe aqueous phase was re-extracted with EA (200 ml)
4. customdried
5. customevaporated in vacuo
6. customto give a brown oil
7. customPurification by FCC
8. washeluting with CX-ER (1:1)

ORD record

ord-846babb93fdc4f708dd72afc1c9e8d3d

Source dataset

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04730008