Iodoethane → Methyl acetate hexane

HRID 237861Notes

Reaction equation

[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]#[C:12][CH2:13][OH:14].I[CH2:16][CH3:17]>CN(C=O)C>[CH3:8][O:3][C:4]([CH3:5])=[O:9].[CH3:4][CH2:5][CH2:6][CH2:7][CH2:16][CH3:17].[CH2:16]([O:14][CH2:13][C:12]#[C:11][CH2:10][O:9][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][O:3]1)[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

An oven dried 500 ml RBF was charged with NaH (60% in mineral oil) (1.41 g, 35.3 mmol) and suspended in DMF (100 mL). The mixture was cooled to 0° C. and 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol (prepared in accordance with the procedures of Tamaru et al., Bull. Chem. Soc. Jpn., 1995, 1689-1705) (6.0 g, 35.3 mmol) was added. The reaction mixture was allowed to reach room temperature and stirred for one hour. To the mixture was added iodoethane (20.8 g, 133 mmol). The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O and extracted with MeOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (1-20% MeOAc/hexane) provided 4.71 g of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran as a clear oil.

Workup

customAn oven dried 500 ml RBF
addition, 1995, 1689-1705) (6.0 g, 35.3 mmol) was added
customto reach room temperature
stirringThe reaction mixture was stirred for 3.5 hours at room temperature
custombefore being quenched with ice/H2O
extractionextracted with MeOAc
washThe organic phase was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-fd436759d4e74f2f98770a0ccab266a0
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642603B2

Reaction notes

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