Acetaldehyde → HCID 69521107, compound

HRID 1374908Notes

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].C([Li])CCC.[CH:20](=[O:22])[CH3:21].O>O1CCCC1>[OH:22][CH:20]([C:4]#[C:3][C:2]([N:6]1[Si:7]([CH3:14])([CH3:13])[CH2:8][CH2:9][Si:10]1([CH3:11])[CH3:12])([CH3:1])[CH3:5])[CH3:21]

Participants

Conditions

Temperature: -20 °C

Procedure

1-(1,1-Dimethyl-2-propynyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane (1.0 g) in dry tetrahydrofuran (10 ml) was cooled to −50° C. under an atmosphere of nitrogen with stirring and a solution of n-butyl lithium (2.0 ml, 2.5M solution in hexanes) was added dropwise over 2 minutes. The mixture was stirred for 0.25 hour at −50° C., allowed to warm to −20° C. then acetaldehyde (0.22 g) in tetrahydrofuran (2 ml) was added dropwise. The reaction was stirred at −20° C. for 1.5 hours, allowed to warm to ambient temperature over 1 hour and treated with water. The product was extracted with ethyl acetate (three times) and the extracts were combined, washed with water (twice) then dried over magnesium sulphate and evaporated under reduced pressure to give (2-hydroxy-5-methylhex-3-yn-5-yl)- 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane,1.06 g, as a yellow liquid.

Workup

stirringThe mixture was stirred for 0.25 hour at −50° C.
stirringThe reaction was stirred at −20° C. for 1.5 hours
temperatureto warm to ambient temperature over 1 hour
extractionThe product was extracted with ethyl acetate (three times)
washwashed with water (twice)
dry with materialthen dried over magnesium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-2bc84ad185394f749cc93899c30004fe
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166621B2

Reaction notes

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