Diethyl (cyanomethyl)phosphonate → HCID 66959138, compound

HRID 1367739Notes

Reaction equation

HRID 1367739 reaction equation
[C:1]([Si:5]([CH3:29])([CH3:28])[O:6][C:7]1[C:8]([CH2:26][CH3:27])=[CH:9][C:10]2[CH:11]3[CH:19]([CH2:20][CH2:21][C:22]=2[CH:23]=1)[CH:18]1[C:14]([CH3:25])([C:15](=O)[CH2:16][CH2:17]1)[CH2:13][CH2:12]3)([CH3:4])([CH3:3])[CH3:2].C(OP([CH2:38][C:39]#[N:40])(=O)OCC)C>>[C:1]([Si:5]([CH3:29])([CH3:28])[O:6][C:7]1[C:8]([CH2:26][CH3:27])=[CH:9][C:10]2[CH:11]3[CH:19]([CH2:20][CH2:21][C:22]=2[CH:23]=1)[CH:18]1[C:14]([CH3:25])([C:15](=[CH:38][C:39]#[N:40])[CH2:16][CH2:17]1)[CH2:13][CH2:12]3)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 66960001HCID 66960001, compound

Product 1

HCID 66959138HCID 66959138, compoundYield 57%

Procedure

The reaction was carried out as described in procedure C using silyl ether 12 (1 g, 2.6 mmol) and diethyl(cyanomethyl)phosphonate (691 mg, 631 μl, 3.9 mmol). Flash column chromatography (SiO2 hexane:ethyl acetate 20:1) afforded the two isomers 24 as a colourless oil (641 mg, 1.47 mmol, 57%). m/z (FAB) 435.3 (M+, 100%); HRMS (FAB+) calcd for C28H41ONSi 435.2957, found 435.2961.

Sources & evidence

ORD record
ord-95b63737bf584f569d7eec5fbb5bf9ca
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

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