Sodium borohydride → HCID 54511055, compound

HRID 1076026Notes

Reaction equation

HRID 1076026 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]=[CH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[O:6][C:5]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54326860HCID 54326860, compound

Product 1

HCID 54511055HCID 54511055, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

IX (1.65 g, 0.008 mole) was dissolved in absolute ethanol (200 ml), and the solution was cooled to 0°C. Sodium tetrahydroborate (0.70 g, 0.0185 mole) was added in one portion with stirring. The turbid solution was stirred at 0°-5°C for 15 minutes and then at room temperature for 20 hours. The solution was concentrated to 1/4 of the volume by distillation from a water bath (40°C) under reduced pressure (50 mm Hg). The residual solution was cooled to 10°C, and then cold water (800 ml) and N sodium hydroxide (25 ml) were added successively with stirring. The stirring was continued for 15 minutes at room temperature and then the pH of the emulsion was adjusted to 7.8 by addition of 3N acetic acid. The reaction mixture was extracted with two 150-ml portions of ether. The combined organic extracts were washed with water (100 ml) and dried over magnesium sulfate. The ethereal solution was evaporated to dryness from a water bath (60°C) under reduced pressure, at last under 15 mm Hg. The residual oil (1.67 g) was purified by distillation under nitrogen. 1.13 g (68%) of X were hereby obtained as a yellow liquid, b0.2 97°-99°C, nD20 1.5166.

Workup

  1. stirringThe turbid solution was stirred at 0°-5°C for 15 minutes
  2. concentrationThe solution was concentrated to 1/4 of the volume by distillation from a water bath (40°C) under reduced pressure (50 mm Hg)
  3. temperatureThe residual solution was cooled to 10°C
  4. additioncold water (800 ml) and N sodium hydroxide (25 ml) were added successively
  5. stirringwith stirring
  6. waitThe stirring was continued for 15 minutes at room temperature
  7. additionthe pH of the emulsion was adjusted to 7.8 by addition of 3N acetic acid
  8. extractionThe reaction mixture was extracted with two 150-ml portions of ether
  9. washThe combined organic extracts were washed with water (100 ml)
  10. dry with materialdried over magnesium sulfate
  11. customThe ethereal solution was evaporated to dryness from a water bath (60°C) under reduced pressure
  12. distillationThe residual oil (1.67 g) was purified by distillation under nitrogen
  13. custom1.13 g (68%) of X were hereby obtained as a yellow liquid, b0.2 97°-99°C

Sources & evidence

ORD record
ord-019d0bff01d040cf8ca92393d8b26184
Source dataset
uspto-grants-1976_05
Patent number
US03954813

Reaction notes

Loading…