Water → HCID 21078360, compound
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]>C1COCC1>[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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 THF (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., then formaldehyde gas was bubbled through the mixture until no starting material remained, as determined by glc analysis. On complete reaction the mixture was treated with water, the ether phase separated and the aqueous phase was extracted with ethyl acetate (twice). The organic extracts were combined, washed with water (three times), dried over magnesium sulphate and evaporated to give 1-(1,1-dimethyl-4-hydroxy-2-butynyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane as a pale yellow liquid (24.96 g).
Workup
- stirringThe mixture was stirred for 0.5 hour
- customformaldehyde gas was bubbled through the mixture until no starting material
- customOn complete reaction the mixture
- customthe ether phase separated
- extractionthe aqueous phase was extracted with ethyl acetate (twice)
- washwashed with water (three times)
- dry with materialdried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-77b12990431d48e78b7aeb4661f148dc
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067592B2
Reaction notes
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