Water → HCID 10965171, compound

HRID 984507Notes

Reaction equation

HRID 984507 reaction equation
[CH3:1]C(C[AlH]CC(C)C)C.[C:10]([Si:16]1([CH3:20])[CH2:19][CH2:18][CH2:17]1)#[C:11][CH2:12][CH2:13][CH2:14][CH3:15].[F-].[Na+].O>CCCCCC.CCOCC.C(Cl)Cl>[CH:10](/[Si:16]1([CH3:20])[CH2:17][CH2:18][CH2:19]1)=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH3:1]

Participants

8

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 14487Diisobutylaluminum hydrideHCID 22559337HCID 22559337, compound

Product 1

HCID 10965171HCID 10965171, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Neat DIBAL-H (1.93 mL, 1.52 g, d=0.789, 10.7 mmol, 1.2 equiv) was added to a solution of 1-(1-hexynyl)-1-methylsilacyclobutane (1.62 g, 9,0 mmol) in hexane (14 mL) and Et2O (9 mL) at 0° C. The mixture was stirred for 3 h at 0° C., 9 h at rt, and then was diluted with CH2Cl2 (40 mL). Solid NaF (3.21 g, 76.4 mmol, 8.5 equiv) was added, followed by H2O (2.9 mL, 161 mmol, 17.8 equiv) and the suspension was stirred for 3 h, then was filtered and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (SiO2, pentane) and Kugelrohr distillation to afford 1.35 g (82%) of (Z)-1 as a colorless oil.

Workup

  1. stirringthe suspension was stirred for 3 h
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. distillationThe crude product was purified by column chromatography (SiO2, pentane) and Kugelrohr distillation
  5. customto afford 1.35 g (82%) of (Z)-1 as a colorless oil

Sources & evidence

ORD record
ord-2140a017a1bc434f93e9b08a892dd15c
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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