Sodium borohydride → HCID 53257212, compound

HRID 1502547Notes

Reaction equation

HRID 1502547 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-8c436dbeed044e2ba81e5e3f0b2482ad
Source dataset
uspto-grants-2015_12
Patent number
US09206230B2

Reaction notes

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