Sodium borohydride → HCID 178500963, compound

HRID 1005340Notes

Reaction equation

HRID 1005340 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:10][C:9](=[C:11]([C:22]([O:24][CH3:25])=[O:23])[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8]1)=[O:6]>O1CCCC1>[CH3:3][O:4][C:5]([C@@H:7]1[CH2:10][C@H:9]([CH:11]([C:22]([O:24][CH3:25])=[O:23])[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53890802HCID 53890802, compound

Product 1

HCID 178500963HCID 178500963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (4.28 g, 0.11 mol) was added portionwise to a stirred solution of benzyl methyl 3-methoxycarbonylcyclobutylidenemalonate (30 g, 0.09 mol) in dry tetrahydrofuran (200 ml) cooled to 0° C. The cooling bath was then removed and after 20 minutes water (300 ml) was added. The mixture was extracted with diethyl ether (3×200 ml) and the combined extracts washed with brine solution. The organic phase was dried, filtered and evaporated to a colourless oil (27.0 g). Chromatography on flash silica eluting with hexane-ether (9:1 then 8:2 then 7:3) gave the title compound as a colourless oil).

Workup

  1. customThe cooling bath was then removed and after 20 minutes water (300 ml)
  2. additionwas added
  3. extractionThe mixture was extracted with diethyl ether (3×200 ml)
  4. washthe combined extracts washed with brine solution
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated to a colourless oil (27.0 g)

Sources & evidence

ORD record
ord-6089401835834e4faad39fe4033848a3
Source dataset
uspto-grants-2000_04
Patent number
US06054448

Reaction notes

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