Sodium borohydride → HCID 18630372, compound

HRID 368602Notes

Reaction equation

HRID 368602 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]([CH2:20][CH3:21])[C:6](=[O:19])[C:7]1[C:12]([CH:13]=[O:14])=[CH:11][CH:10]=[CH:9][C:8]=1[Si:15]([CH3:18])([CH3:17])[CH3:16])[CH3:4]>C(O)C.CCOCC>[CH2:20]([N:5]([CH2:3][CH3:4])[C:6](=[O:19])[C:7]1[C:12]([CH2:13][OH:14])=[CH:11][CH:10]=[CH:9][C:8]=1[Si:15]([CH3:17])([CH3:16])[CH3:18])[CH3:21]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 14528629HCID 14528629, compound

Product 1

HCID 18630372HCID 18630372, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium borohydride (1.0 g, 26.4 mmol) was added to a solution of N,N-diethyl-2-trimethylsilyl-6-formylbenzamide, prepared in Example 97, (5.54 g, 20 mmol) in absolute ethanol (100 mL). After 3 h the mixture was diluted with ether, extracted three times with brine, dried (MgSO4), concentrated, and recrystallized from 1:1 ethyl acetate/hexanes to afford 4.12 g of N,N-diethyl-2-trimethylsilyl-6-hydroxymethylbenzamide as a white solid, a 74% yield. m.p. 81-82.5° C.

Workup

  1. extractionextracted three times with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customrecrystallized from 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-df4e350706cd486b9759de6eb18e6fc7
Source dataset
uspto-grants-2000_10
Patent number
US06133252

Reaction notes

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