Water → (E)-4-[3-Methoxy-4-(methoxymethoxy)phenyl]-3-buten-1-ol

n-Butyllithium (1.6M in hexane, 25 ml) was added dropwise to a stirred suspension of (3-hydroxypropyl)triphenylphosphonium bromide (8.03 g) in dry THF (50 ml) cooled to 0° under nitrogen. The resulting blood-red solution was stirred at 0° for 10 min and then 3-methoxy-4-(methoxymethoxy)-benzaldehyde (3.60 g) in dry THF (10 ml) was added dropwise over 5 min. The mixture was allowed to warm to room temperature, stirred for 4 h, water (10 ml) was added and the majority of the solvent was removed in vacuo at 40°. A solution of the residual oil in ER (200 ml) was washed with water (150 ml), dried, treated with charcoal, concentrated and purified by FCC eluting with EA-H (1:1) to give the title compound (1.55 g). T.l.c. (EA-H 1:1) Rf 0.30.

1. temperaturecooled to 0° under nitrogen
2. stirringstirred for 4 h
3. customthe majority of the solvent was removed in vacuo at 40°
4. washA solution of the residual oil in ER (200 ml) was washed with water (150 ml)
5. customdried
6. additiontreated with charcoal
7. concentrationconcentrated
8. custompurified by FCC
9. washeluting with EA-H (1:1)

ORD record

ord-6969517f20b34f40ad438433119293c4

Source dataset

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04730008