Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[CH:10].C([Li])CCC.CN(C)P(=O)(N(C)C)N(C)C.[C:27]([Si:31]([O:34][CH2:35][CH:36]1[CH2:38][CH:37]1[CH2:39][CH2:40]Br)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28].[Cl-].[NH4+]>O1CCCC1>[Si:31]([O:34][CH2:35][CH:36]1[CH2:38][CH:37]1[CH2:39][CH2:40][C:10]#[C:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:32])[CH3:33]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A tetrahydrofuran solution (15 ml) of propargyl alcohol tetrahydropyranyl ether (1.44 g, 10.3 mmol) was cooled to -78° C., and butyllithium (factor=1.5, 6.9 ml, 10.3 mmol) was added thereto. Fifteen minutes later, the temperature was raised to 0° C. Hexamethylphosphoric triamide (3.76 ml, 21 mmol) was added thereto, and the mixture was stirred for 15 minutes. A tetrahydrofuran solution of 2-(2-bromoethyl)cyclopropylmethyl t-butyldimethyl silyl ether (2.73 g, 10.3 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. A saturated ammonium chloride solution was added thereto, and the product was extracted with ethyl ether. The crude product was purified by silica gel column chromatography to obtain 2-(5-tetrahydropyranyloxy-3-pentynyl)cyclopropylmethyl t-butyldimethylsilyl ether (3 g).
Workup
- stirringthe mixture was stirred at room temperature for 2 hours
- extractionthe product was extracted with ethyl ether
- customThe crude product was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-95a8518022b348ec9a34488da3a803fd
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05416231
Linked notes
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