Methanol → (1s,3s)-3-(Benzyloxy)cyclobutan-1-ol

HRID 1051688Notes

Reaction equation

HRID 1051688 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][C:11](=[O:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.CO.[BH4-].[Na+]>O>[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([OH:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 149327873-(Benzyloxy)cyclobutan-1-one

Product 1

HCID 22609921(1s,3s)-3-(Benzyloxy)cyclobutan-1-olYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 100-mL round-bottom flask was charged with 3-(benzyloxy)cyclobutanone (2.00 g, 11.4 mmol), tetrahydrofuran (20 mL), and methanol (1 mL), and the solution was cooled to 0° C. Sodium borohydride (0.475 g, 12.5 mmol) was added portionwise, and the resulting mixture stirred for 30 min at room temperature. The reaction mixture was poured into water (30 mL), and extracted with ethyl acetate (2×30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-(benzyloxy)cyclobutanol (1.83 g, 90%) as yellow oil. MS (ESI, pos. ion) m/z 179 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25a83347b8ab4df3902ebcfecef2cc56
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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