Aluminium lithium hydride → HCID 22797560, compound

HRID 2397953Notes

Reaction equation

HRID 2397953 reaction equation
[OH:1][C@@H:2]1[C@@:35]2([CH3:36])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:30])[CH2:15][CH2:16][C@H:17]([O:21]C(=O)C2C=CC=CC=2)[CH:18]([CH3:20])[CH3:19])[CH2:5][C@@H:4]([O:38]C(=O)C2C=CC=CC=2)[CH2:3]1.O[C@@H]1[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2[C@H](C)CCC(OC(=O)C2C=CC=CC=2)C(C)C)C[C@@H](OC(=O)C2C=CC=CC=2)C1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[OH:1][C@@H:2]1[C@@:35]2([CH3:36])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:30])[CH2:15][CH2:16][C@H:17]([OH:21])[CH:18]([CH3:20])[CH3:19])[CH2:5][C@@H:4]([OH:38])[CH2:3]1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 22797575HCID 22797575, compoundHCID 70634867HCID 70634867, compound

Product 1

HCID 22797560HCID 22797560, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1α-Hydroxy-3β,24(S)-dibenzoyloxy-cholest-5-ene prepared in the same way as in Example 4, (B) was reduced with LiAlH4 in dry diethyl ether to form 1α,3β,24(S)-trihydroxy cholest-5-ene. This product (180 mg) was then reacted with 24 ml. of acetic anhydride and 75 ml. of pyridine at 95° C. for 3.5 hours. The product was treated in the same way as in Example 3, (A), and chromatographed through a column containing silica gel as a carrier to afford 195 mg of 1α,3β,24(S)-triacetoxy-cholest-5-ene.

Sources & evidence

ORD record
ord-4c730a30641446bfb0ca2d26682f91fe
Source dataset
uspto-grants-1977_05
Patent number
US04022891

Reaction notes

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