Aluminium lithium hydride → HCID 70167784, compound

HRID 1385620Notes

Reaction equation

HRID 1385620 reaction equation
[CH3:1][C:2]([Si:5]([CH3:32])([CH3:31])[O:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([C:17]([CH3:30])([CH3:29])[C:18](=[O:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]([Si:5]([CH3:32])([CH3:31])[O:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([C:17]([CH3:30])([CH3:29])[C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70167532HCID 70167532, compound

Product 1

HCID 70167784HCID 70167784, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

ix)—A solution of compound 9 (39.4 g) in dry tetrahydrofuran (400 ml) was added dropwise to an ice-cooled suspension of lithium aluminium hydride (9.81 g) in tetrahydrofuran (490 ml). The mixture was stirred at room temperature for 1 h. The reaction was cooled to 0° C., and then quenched with a saturated aqueous solution of sodium sulfate. The reaction mixture was filtered over celite and the filtrate concentrated under reduced pressure to give (3β,20S)-20-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4-dimethylpregn-5-en-3-ol (compound 10: 38.9 g), which was used in the following step without further purification.

Workup

  1. temperaturecooled
  2. temperatureThe reaction was cooled to 0° C.
  3. customquenched with a saturated aqueous solution of sodium sulfate
  4. filtrationThe reaction mixture was filtered over celite
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-0fb9c1b84d1746eea47702772ce96a3b
Source dataset
uspto-grants-2001_07
Patent number
US06262282B1

Reaction notes

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