Iodine → (3-(Benzyloxy)cyclobutyl)methanol

HRID 1966836Notes

Reaction equation

HRID 1966836 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([C:13](O)=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].II>O1CCCC1>[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 4311764Sodium borohydrideHCID 128151113-(Benzyloxy)cyclobutane-1-carboxylic acid

Product 1

HCID 15221213(3-(Benzyloxy)cyclobutyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A tetrahydrofuran solution of 3-(benzyloxy)cyclobutanecarboxylic acid (2.5 gm, 11.36 mmol) was added to a solution of sodium borohydride (0.52 gm, 13.63 mmol) in tetrahydrofuran. Iodine (1.44 gm, 5.68 mmol) in tetrahydrofuran solution was added to solution at 0° C., after about 15 minutes, and the mixture was stirred at room temperature for about 2 hours. It was quenched with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with dilute sodium hydroxide solution and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get the title compound.

Workup

  1. customIt was quenched with dilute hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with dilute sodium hydroxide solution and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1263694c9f9436bb2526f1ed6162031
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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