Sodium borohydride → HCID 178521639, compound

HRID 1369442Notes

Reaction equation

HRID 1369442 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-fc9d55e2b23d4bcb80fa92cfeae946c7
Source dataset
uspto-grants-2003_06
Patent number
US06579875B1

Reaction notes

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