Sodium borohydride → HCID 53980569, compound

HRID 2071662Notes

Reaction equation

HRID 2071662 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH:16]=[CH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:12]1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH:16]=[CH:17][CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:12]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86735058HCID 86735058, compound

Product 1

HCID 53980569HCID 53980569, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

III (3.17 g, 0.00900 mole) was dissolved in methanol (75 ml) and sodium tetrahydroborate (1.7 g, 0.045 mole) was added at 0° C with stirring. The stirring was continued for 1 hour. During this time the temperature was slowly raised to room temperature. The colourless solution was poured into ice-water (250 ml) and extracted with ether (100 + 50 + 50 ml). The combined ethereal extracts were washed with water (50 + 25 + 25 ml), dried over magnesium sulfate, and evaporated from a water bath (50° C, 10 mm Hg). The obtained light yellowish oil (3.38 g) was distilled under reduced pressure to give 2.90 g (91%) of IV as a colourless oil, b0.05 175°-188° C, nD25 1.4699.

Workup

  1. extractionextracted with ether (100 + 50 + 50 ml)
  2. washThe combined ethereal extracts were washed with water (50 + 25 + 25 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated from a water bath (50° C, 10 mm Hg)
  5. distillationThe obtained light yellowish oil (3.38 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-4a38dc82a5794c91ae33b7fe3bcef59f
Source dataset
uspto-grants-1977_09
Patent number
US04048198

Reaction notes

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