Diethyl aluminum cyanide → HCID 57026814, compound

HRID 1764976Notes

Reaction equation

HRID 1764976 reaction equation
[CH3:1][CH:2]([C@H:4]([CH:6]=[CH:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C:14]3[CH2:15][CH2:16][C:17]4[C@:22]([C:24]=3[CH2:25][CH2:26]2)([CH3:23])[CH2:21][CH2:20][C:19](=[O:29])[CH:18]=4)[CH2:12][CH2:11]1)[CH3:9])[CH3:5])[CH3:3].[C-:30]#[N:31].C([Al+]CC)C>>[C:30]([C@:17]12[CH2:18][C:19](=[O:29])[CH2:20][CH2:21][C@:22]1([CH3:23])[C:24]1[CH2:25][CH2:26][C@@:27]3([CH3:28])[C@@H:13]([CH2:12][CH2:11][C@@H:10]3[C@H:8]([CH3:9])[CH:7]=[CH:6][C@H:4]([CH3:5])[CH:2]([CH3:1])[CH3:3])[C:14]=1[CH2:15][CH2:16]2)#[N:31]

Participants

3

Reactant 2

HCID 16686413Diethyl aluminum cyanideHCID 57222965HCID 57222965, compound

Product 1

HCID 57026814HCID 57026814, compound

Procedure

1.54 g ergosta-4,8,22-trien-3-one were treated with 11.73 ml diethylaluminum cyanide solution (1 N, toluene) as described in example 58. After aqueous work up and chromatography 0.90 g 5-cyano-5α-ergosta-8,22-dien-3-one were isolated as a white solid (beside the corresponding 5β-cyano-compound).

Sources & evidence

ORD record
ord-47b800ba6ddf485caa752818ce3c2ab2
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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