Sodium borohydride → HCID 66603674, compound

HRID 573964Notes

Reaction equation

HRID 573964 reaction equation
[CH2:1]([O:23][C:24]1[CH:31]=[C:30]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH:29]=[CH:28][C:25]=1[CH:26]=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[BH4-].[Na+]>O1CCCC1.CO>[CH2:1]([O:23][C:24]1[CH:31]=[C:30]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH:29]=[CH:28][C:25]=1[CH2:26][OH:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 715790322,4-Bis(docosyloxy)benzaldehyde

Product 1

HCID 66603674HCID 66603674, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Under an argon atmosphere, 2,4-bis(docosyloxy)benzaldehyde (2.99 g, 3.96 mmol) was dissolved in a mixed solvent of dehydrating tetrahydrofuran (60 mL) and methanol (6.0 mL), sodium borohydride (375 mg, 9.91 mmol) was added, and the mixture was stirred at 40° C. for 2 hr. After completion of the reaction, purified water (2.0 mL) was added dropwise to decompose unreacted sodium borohydride and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure, methanol was added, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to give the title compound (2.77 g, 92.9%) as a white solid.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. custompurified water (2.0 mL)
  4. additionwas added dropwise
  5. filtrationthe mixture was filtered through celite
  6. concentrationThe filtrate was concentrated under reduced pressure, methanol
  7. additionwas added
  8. filtrationthe precipitated solid was collected by filtration
  9. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-ecc1c749ed624a1cbe9465fcf8dc3cfc
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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