Sodium borohydride → HCID 69529639, compound

HRID 1529845Notes

Reaction equation

HRID 1529845 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][C@:9]12[CH2:17][CH2:16][C:15]3[C:18]4[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[CH:22][C:23]=4[CH2:24][CH2:25][C:14]=3[C@@H:13]1[CH2:12][CH2:11][C:10]2=[O:28].[BH4-].[Na+]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][C@:9]12[CH2:17][CH2:16][C:15]3[C:18]4[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[CH:22][C:23]=4[CH2:24][CH2:25][C:14]=3[C@@H:13]1[CH2:12][CH2:11][CH:10]2[OH:28]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86601514HCID 86601514, compound

Product 1

HCID 69529639HCID 69529639, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the ketone 50 (58.0 g, 0.145 mol) in methyl alcohol (1 L) was added by portion NaBH4 (5.5 g, 0.145 mol) at 0° C. The solution was stirred for 20 min then quenched with saturated aqueous NH4Cl solution (500 mL); and methanol was evaporated. The residue was diluted with ethyl acetate (1 L) and washed with brine, dried over magnesium sulfate and rotary evaporated to give 55.6 g (95%) of crude product 51.

Workup

  1. customthen quenched with saturated aqueous NH4Cl solution (500 mL)
  2. customand methanol was evaporated
  3. additionThe residue was diluted with ethyl acetate (1 L)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customrotary evaporated

Sources & evidence

ORD record
ord-f03d26ff518449078f31860e53cf3f0d
Source dataset
uspto-grants-2015_07
Patent number
US09090651B2

Reaction notes

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