Hydrochloric Acid → (2S,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadien-1-ol
Reaction equation
CC([Si]([O:8][CH2:9][C@H:10]([CH3:28])[C@@H:11]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C@@H:12]([CH3:17])/[CH:13]=[CH:14]\[CH:15]=[CH2:16])(C)C)(C)C.Cl>C1COCC1>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][O:18][C@@H:11]([C@@H:12]([CH3:17])/[CH:13]=[CH:14]\[CH:15]=[CH2:16])[C@@H:10]([CH3:28])[CH2:9][OH:8])=[CH:25][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (1,1-dimethylethyl)[[(2S,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadienyl]oxy]dimethylsilane (6.74 g, 16.68 mmol) and THF (70 mL) is cooled to 0° C. 4 N aqueous HCl (70 mL) is added to the solution dropwise to maintain the reaction temperature at less than 5° C. The mixture is stirred at 0° C. for 1 h. The mixture is quenched by the addition of saturated aqueous NaCO3. The organic phase is separated. The aqueous phase is extracted with ethyl acetate (5×100 mL). The combined organic phase is washed with brine, dried over NaSO4 and concentrated. Flash chromatography gives the desired compound (4.17 g, 86%) as a clear oil.
Workup
- temperatureto maintain the reaction temperature at less than 5° C
- customThe mixture is quenched by the addition of saturated aqueous NaCO3
- customThe organic phase is separated
- extractionThe aqueous phase is extracted with ethyl acetate (5×100 mL)
- washThe combined organic phase is washed with brine
- dry with materialdried over NaSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9a7a5e6f6be048018575e6809d578f33
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148218B2
Reaction notes
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