Sodium borohydride → HCID 53257212, compound

HRID 537617Notes

Reaction equation

HRID 537617 reaction equation
[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][O:65][C:66]2[C:73]([O:74][CH3:75])=[CH:72][C:69]([CH:70]=[O:71])=[CH:68][C:67]=2[O:76][CH3:77])[CH2:21]1)[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][CH3:18].[BH4-].[Na+]>C1COCC1>[CH3:75][O:74][C:73]1[CH:72]=[C:69]([CH:68]=[C:67]([O:76][CH3:77])[C:66]=1[O:65][CH2:64][CH:22]1[CH2:21][CH:20]([O:19][CH2:1][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][CH3:18])[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23]1)[CH2:70][OH:71]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86654895HCID 86654895, compound

Product 1

HCID 53257212HCID 53257212, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

4-[3′,4′,5′-Tris(octadecyloxy)cyclohexylmethyloxy]-3,5-dimethoxybenzaldehyde (73 mg, 0.07 mmol) was dissolved in THF (2 ml), 4 equivalents of sodium borohydride was added, and the mixture was stirred at 40° C. for 3 hr. The solvent was evaporated, and chloroform was added. The mixture was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate solution and saturated brine. The solvent of the organic layer was evaporated, and acetonitrile was added. The precipitate was collected by filtration and dried to give 3,5-dimethoxy-4-[3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy]benzyl alcohol (70 mg, 0.06 mmol).

Workup

  1. customThe solvent was evaporated
  2. additionchloroform was added
  3. washThe mixture was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate solution and saturated brine
  4. customThe solvent of the organic layer was evaporated
  5. additionacetonitrile was added
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a04b291f08d5442c84fb6b3bb94c563c
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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