Water → 7-Dehydrositosterol

HRID 2183425Notes

Reaction equation

HRID 2183425 reaction equation
[CH3:1][CH2:2][C@@H:3]([CH:31]([CH3:33])[CH3:32])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@@:12]2([CH3:30])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:29])[CH2:21][CH2:22][C@H:23]([O:25]C(C)=O)[CH2:24][C:19]4=[CH:18][CH:17]=[C:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH3:1][CH2:2][C@@H:3]([CH:31]([CH3:32])[CH3:33])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@@:12]2([CH3:30])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:29])[CH2:21][CH2:22][C@H:23]([OH:25])[CH2:24][C:19]4=[CH:18][CH:17]=[C:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 117194496020-61-7HCID 21226445Aluminium lithium hydride

Product 1

HCID 52836347-Dehydrositosterol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 7-dehydrositosterol acetate (6) (2.5 g, 5.5 mmol) in dry ether (200 mL) was added lithium aluminum hydride (2.09 g, 55.0 mmol). The reaction mixture was stirred at room temperature for 2 h, then cooled with an ice-water bath and the excess water (5 mL). After 30 minutes, ether (100 mL) was added and filtered. The cake was washed with ether (2×100 mL) and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 7-dehydrositosterol (7) in quantitative yield.

Workup

  1. temperaturecooled with an ice-water bath
  2. waitAfter 30 minutes
  3. filtrationfiltered
  4. washThe cake was washed with ether (2×100 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d8250c3b45d461386ed1931d4fc543f
Source dataset
uspto-grants-2005_05
Patent number
US06900191B1

Reaction notes

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