Water → HCID 21078360, compound

HRID 916540Notes

Reaction equation

[CH3:1][C:2]([N:6]1[Si:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][Si:7]1([CH3:14])[CH3:13])([CH3:5])[C:3]#[CH:4].[CH2:15]([Li])CCC.[OH2:20]>O1CCCC1>[CH3:5][C:2]([N:6]1[Si:7]([CH3:14])([CH3:13])[CH2:8][CH2:9][Si:10]1([CH3:11])[CH3:12])([CH3:1])[C:3]#[C:4][CH2:15][OH:20]

Participants

Conditions

Temperature: -20 °C

Procedure

1-(1,1-Dimethyl-2-propynyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane (22.6 g) in dry tetrahydrofuran (250 ml) was cooled to −50° C. under an atmosphere of nitrogen with stirring and a solution of n-butyl lithium (44 ml, 2.5M solution in hexanes) was added dropwise over 10 minutes. The mixture was stirred for 0.5 hour, allowed to warm to −20° C. and formaldehyde gas bubbled through the mixture until no starting material remained, as determined by glc analysis. On completion of the reaction, the mixture was treated with water, the ether phase separated, the aqueous phase extracted with ethyl acetate (twice) and the organic extracts combined and washed with water (three times). The combined organic extract was dried over magnesium sulphate and evaporated under reduced pressure to give 4-methyl-4-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)pent-2-yn-1-ol (24.96 g) as a pale yellow liquid.

Workup

stirringThe mixture was stirred for 0.5 hour
customformaldehyde gas bubbled through the mixture until no starting material
customOn completion of the reaction
customthe ether phase separated
extractionthe aqueous phase extracted with ethyl acetate (twice) and the organic extracts
washwashed with water (three times)
extractionThe combined organic extract
dry with materialwas dried over magnesium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-129edcc683554f1bb3dade2af5756737
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271130B2

Reaction notes

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