Reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][O:10][C:11]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12].[I:19][CH2:20]I.O>O1CCCC1>[CH3:9][O:10][C:11]([C:13]1([CH2:20][I:19])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium diisopropylamide (10.9 ml of 2.0M solution in heptane/tetrahydrofuran/ethylbenzene) was added to a stirred solution of tetrahydropyran-4-carboxylic acid methyl ester (3.00 g) in tetrahydrofuran (50 ml) at 0° C. under an atmosphere of nitrogen. The mixture was stirred for 30 minutes before dropwise addition of diiodomethane (2.51 ml). Stirring was continued for a further hour during which it warmed to room temperature. The reaction was poured into water (50 ml) and then extracted with diethyl ether (3×40 ml). The combined organics were washed with water (2×20 ml), 2 M hydrochloric acid (20 ml), water (20 ml) and brine (20 ml). After drying (MgSO4), filtering and evaporating under reduced pressure a yellow oil was obtained which was purified by column chromatography eluting with 3.1 hexane/diethyl ether to give the title compound as a colourless oil (3.11 g, 53%).
Workup
- waitwas continued for a further hour during which it
- extractionextracted with diethyl ether (3×40 ml)
- washThe combined organics were washed with water (2×20 ml), 2 M hydrochloric acid (20 ml), water (20 ml) and brine (20 ml)
- dry with materialAfter drying (MgSO4)
- filtrationfiltering
- customevaporating under reduced pressure a yellow oil
- customwas obtained which
- customwas purified by column chromatography
- washeluting with 3.1 hexane/diethyl ether
Sources & evidence
- ORD record
- ord-cf4f3324b8dd4eedbca6d88137116b8c
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809100B2
Linked notes
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