Lithium Hydroxide → (E)-6-(tert-butyldimethylsilyloxy)hex-2-enoic acid
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[C:14]([O:16]CC)=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.CO.O>[Si:1]([O:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Procedure
To a solution of (E)-ethyl 6-(tert-butyldimethylsilyloxy)hex-2-enoate (7) (27.2 g, 0.1 mol) in THF and MeOH was added LiOH (6.6 g, 0.3 mol) in 50 mL H2O, the mixture was stirred at RT for 5 hours. After removal of the solvent, the residue was poured into 3N HCl to the pH value was adjusted to 4-5, then extracted with DCM (250 mL×2), and the organic layers were washed with water (250 mL×3) and brine (3×200 mL), dried over Na2SO4 and concentrated to give the desired compound of (E)-6-(tert-butyldimethylsilyloxy)hex-2-enoic acid (8) (12.1 g, 50%) as a yellow oil after purification by column chromatography on silica gel (eluent: PE:EA=5:1). 1H NMR (300 MHz, CDCl3): δ 0.0021 (S, 6H), 0.0857 (S, 9H), 1.600 (m, 2H), 1.197 (t, 3H), 2.240 (q, 2H), 3.586 (t, 2H), 5.832 (d, J=15.6 Hz, 1H), 6.936-6.885 (m, 1H); LC-MS found 245 (M+H)+.
Workup
- customAfter removal of the solvent
- additionthe residue was poured into 3N HCl to the pH value
- extractionextracted with DCM (250 mL×2)
- washthe organic layers were washed with water (250 mL×3) and brine (3×200 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3994913fd89848669fe9054371aad8f4
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09265734B2
Reaction notes
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