Sodium borohydride → HCID 10902156, compound

HRID 582902Notes

Reaction equation

HRID 582902 reaction equation
[O:1]1[C@H: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])[C@H:2]1[C:3](OC)=[O:4].[BH4-].[Na+]>O1CCCC1>[O:1]1[C@H: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])[C@H:2]1[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 56999066HCID 56999066, compound

Product 1

HCID 10902156HCID 10902156, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 500 ml of tetrahydrofuran were suspended 62.4 g (0.2 mol) of the methyl (2S,3R)-2,3-epoxyoctadecanoate (V-1) prepared in Example 3-(3) and 7.4 g (0.2 mol) of NaBH4, followed by heat refluxing for 3 hours. After confirming disappearance of the compound (V-1) by TLC, tetrahydrofuran was evaporated. To the residue were added 20 ml of water and then 500 ml of a saturated ammonium chloride aqueous solution to adjust to pH 5 to 6, and the mixture was extracted with 500 ml of ethyl acetate. After drying, ethyl acetate was removed by evaporation, and the resulting crude crystals were recrystallized from heptane to obtain 42.6 g (0.15 mol; yield: 75%) of (2R,3R)-2,3-epoxyoctadecanol (melting point: 77 to 78° C.). Optical rotation [α]D25 =+24.5° (c=0.285, CHCl3)

Workup

  1. temperatureby heat
  2. temperaturerefluxing for 3 hours
  3. customwas evaporated
  4. additionTo the residue were added 20 ml of water
  5. extractionthe mixture was extracted with 500 ml of ethyl acetate
  6. customAfter drying
  7. customethyl acetate was removed by evaporation
  8. customthe resulting crude crystals were recrystallized from heptane

Sources & evidence

ORD record
ord-0b1b40ca4bb641a3a0d2421a717da038
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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