Diethyl Ether → 4-Trimethylsilyl-2,3,5,6-tetrafluorobenzyl alcohol

HRID 34609Notes

Reaction equation

HRID 34609 reaction equation
[CH3:1][Si:2]([CH3:22])([CH3:21])[C:3]1[C:16]([F:17])=[C:15]([F:18])[C:6]([CH2:7][O:8]C2CCCCO2)=[C:5]([F:19])[C:4]=1[F:20].C(OCC)(=O)C.C(OCC)C>CO.Cl>[CH3:1][Si:2]([CH3:22])([CH3:21])[C:3]1[C:16]([F:17])=[C:15]([F:18])[C:6]([CH2:7][OH:8])=[C:5]([F:19])[C:4]=1[F:20]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 139114812-[4-Trimethylsilyl-2,3,5,6-tetrafluorobenzyloxy]-tetrahydropyran

Product 1

HCID 139114824-Trimethylsilyl-2,3,5,6-tetrafluorobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

The crude tetrahydropyranyl ether prepared in Stage (i) was dissolved in methanol (20 cm3), and to the stirred solution was added concentrated hydrochloric acid (3 drops). After stirring for 16 hours at the ambient temperature (ca. 25° C.), the reaction mixture was poured into ethyl acetate, washed with water and brine, and dried. Evaporation of the solvent under reduced pressure gave a yellow oil which was subjected to column chromatography on silica gel using petroleum ether (boiling range 40°-60° C.) containing diethyl ether (10% gradually increased to 40% by volume) as eluent to give 4-trimethylsilyl-2,3,5,6-tetrafluorobenzyl alcohol (0.79 g).

Workup

  1. washwashed with water and brine
  2. customdried
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a yellow oil which
  5. temperaturegradually increased to 40% by volume) as eluent

Sources & evidence

ORD record
ord-c63bc3ba6643468999e4739e9fb348d1
Source dataset
uspto-grants-1988_08
Patent number
US04762835

Reaction notes

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