Acetic Acid → HCID 53961427, compound

HRID 845357Notes

Reaction equation

HRID 845357 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[CH3:6][CH:7]([C@H:9]([CH:11]=[CH:12][C@H:13]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH:23]=C(CC([O-])=O)C=[CH:26]2)=[CH:21][CH:20]=3)[CH2:17][CH2:16]1)[CH3:14])[CH3:10])[CH3:8].[C:38]([OH:41])(=O)[CH3:39]>CO.C(O)C.C(OCC)C>[CH3:8][CH:7]([C@H:9]([CH:11]=[CH:12][C@H:13]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:38]([OH:41])[CH:39]=[CH:26]2)=[CH:21][CH:20]=3)[CH2:17][CH2:16]1)[CH3:14])[CH3:10])[CH3:6]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86742262HCID 86742262, compound

Product 1

HCID 53961427HCID 53961427, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

Calcium chloride (15.0 g) was dissolved in methanol (150 ml) and cooled to -10° C . To a cooled solution was added dropwise while keeping at -10° C. a solution of sodium borohydride (7.5 g) in ethyl alcohol (150 ml) and the solution was stirred at the same temperature for 30 minutes. A solution of ergosta-1,3,5,7,22-pentaen-3-ylacetate (III) (5.0 g) from Example 1 in diethyl ether (100 ml) was added dropwise at a temperature between -5° and -10° C. The reaction mixture was stirred at a temperature between 0° and -5° C. for 3 hrs. and then at room temperature for 3 hrs. 50% Acetic acid was added to prepare a uniform solution and the solution was extracted with ethyl acetate. The extract was washed with water, then an aqueous sodium bicarbonate solution and dried. Ethyl acetate was concentrated and the residue was purified by silica gel chromatography (eluted with chloroform) followed by crystallization with acetone to give 4.2 g (90% yield) of ergosta-1,5,7,22-tetraen-3β-ol (I), m.p. 156°-157° C.

Workup

  1. additionTo a cooled solution was added dropwise
  2. customwhile keeping at -10° C.
  3. stirringThe reaction mixture was stirred at a temperature between 0° and -5° C. for 3 hrs
  4. waitand then at room temperature for 3 hrs
  5. customto prepare a uniform solution
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialan aqueous sodium bicarbonate solution and dried
  9. concentrationEthyl acetate was concentrated
  10. customthe residue was purified by silica gel chromatography (eluted with chloroform)
  11. customfollowed by crystallization with acetone

Sources & evidence

ORD record
ord-0bc7c9e85f5f4918b88e2923de8626cd
Source dataset
uspto-grants-1988_07
Patent number
US04758383

Reaction notes

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