Sodium borohydride → HCID 178521639, compound

HRID 2306601Notes

Reaction equation

HRID 2306601 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.[BH4-].[Na+]>C(O)C>[CH2:1]([O:8][C@@H:9]1[CH2:12][C@H:11]([OH:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 149327873-(Benzyloxy)cyclobutan-1-one

Product 1

HCID 178521639HCID 178521639, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-benzyloxycyclobutan-1-one (0.92 g, 5.22 mmol) (Ogura et al., Bull. Chem. Soc. Jpn., 1984, 57, 1637-1642) and sodium borohydride (0.20 g, 5.29 mmol) in ethanol (15 ml) was stirred at room temperature for 3.5 h. The mixture was filtered, washing with ethanol, and the filtrate was concentrated. Filtration through a plug of silica, eluting with ethyl acetate, gave cis-3-benzyloxy-1-hydroxycyclobutane (0.854 g, 92%) as a colourless oil; 1H NMR (250 MHz, CDCl3) δ1.75-2.00 (2H, m), 2.65-2.79 (2H, m), 3.62 (1H, qn, J=7 Hz), 3.90 (1H, broad qn, J=7 Hz), 4.41 (2H, s), 7.23-7.47 (5H, m).

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with ethanol
  3. concentrationthe filtrate was concentrated
  4. filtrationFiltration through a plug of silica
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-6336f9571a6c40fd8654ee4d4046b9b7
Source dataset
uspto-grants-2004_12
Patent number
US06828322B2

Reaction notes

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