Potassium sodium tartarate → 2,2-Dimethyl-7-(tetrahydro-2H-pyran-2-yloxy)heptan-1-ol
Reaction equation
[CH3:1][C:2]([CH3:20])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C:3](OCC)=[O:4].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[CH3:1][C:2]([CH3:20])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[CH2:3][OH:4]Participants
Procedure
A solution of ethyl 2,2-dimethyl-7-(tetrahydro-2H-pyran-2-yloxy)heptanoate (example 285, step b) (2.22 g) in dry ether (22 mL) at 0° C. under nitrogen, was treated dropwise over 5 minutes with diisobutylaluminium hydride (1M in toluene, 17.1 mL). After 1 hour at 0° C. the reaction mixture was treated cautiously with aqueous potassium sodium tartrate, diluted with ether and the resultant mixture was stirred vigorously for 1.5 hours. The phases were separated and the aqueous phase was extracted with ether (×2). The combined organic phase was washed with water and brine, dried over magnesium sulfate, filtered and evaporated. Purification was by silica gel chromatography eluting with 0 to 50% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless oil. Yield 1.83 g.
Workup
- customThe phases were separated
- extractionthe aqueous phase was extracted with ether (×2)
- washThe combined organic phase was washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customPurification
- washeluting with 0 to 50% ethyl acetate in cyclohexane
Sources & evidence
- ORD record
- ord-149f348ca25b489082b66b13f9feb97f
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629271B2
Reaction notes
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