Hydrochloric Acid → HCID 20253403, compound

HRID 638134Notes

Reaction equation

HRID 638134 reaction equation
[O:1]=[C:2]([CH3:15])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][C:9]#[C:10][CH2:11][C:12]([OH:14])=[O:13].[BH4-].[Na+].Cl>CCO.[Cl-].[Na+].O>[OH:1][CH:2]([CH3:15])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][C:9]#[C:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20253406HCID 20253406, compound

Product 1

HCID 20253403HCID 20253403, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Keto-acid 12 (1.8 g, 8.7 mmol) was dissolved in 25 mL absolute EtOH, and cooled to -20°. NaBH4 (0.456 g, 12 mmol) was added in one portion, and the solution was warmed to 0° over 15 min, then cooled to -20° again. The reaction mixture was then slowly acidified with 3.5N HCl, brine (25 mL) was added, and the solution was extracted with ether (4×25 mL). The combined ether extracts were washed with brine (2×20 mL), dried (MgSO4), and concentrated in vacuo, to give an orange oil, which rapidly darkened in colour. This was used immediately without purification in the next step.

Workup

  1. temperaturecooled to -20°
  2. temperaturethe solution was warmed to 0° over 15 min
  3. temperaturecooled to -20° again
  4. additionwas added
  5. extractionthe solution was extracted with ether (4×25 mL)
  6. washThe combined ether extracts were washed with brine (2×20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give an orange oil, which
  10. customThis was used immediately without purification in the next step

Sources & evidence

ORD record
ord-70693a008a8f499d8861b9b8622284c2
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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