tert-Butanol → tert-Butyl 2-(4-tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetate
Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([OH:18])=[O:17])=[C:12]([CH2:27][CH2:28][CH3:29])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[C:36](O)([CH3:39])([CH3:38])[CH3:37].CCN(CC)CC>C1C=CC=CC=1.CN(C=O)C.C(Cl)Cl.CCOC(C)=O>[Si:1]([O:8][CH2:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([O:18][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:17])=[C:12]([CH2:27][CH2:28][CH3:29])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
To a solution of 929 mg (2.24 mmol) of the product of Step L in benzene were added oxalyl chloride (234 mL, 2.69 mmol) and one drop of DMF at 0° C. The solution was stirred at rt for 45 minutes. After concentration the residue was dissolved in CH2Cl2 (10 mL). The solution was added to a solution of tert-butyl alcohol (253 mL, 2.69 mmol) and Et3N in CH2Cl2 (10 mL) at 0° C. The solution was stirred at rt for 3 hours. The mixture was poured into EtOAc (50 mL) and washed with H2O (1×) and brine, and dried over anhydrous MgSO4. Concentration gave 778 mg of the title compound as a slightly yellow glass.
Workup
- concentrationAfter concentration the residue
- dissolutionwas dissolved in CH2Cl2 (10 mL)
- stirringThe solution was stirred at rt for 3 hours
- washwashed with H2O (1×) and brine
- dry with materialdried over anhydrous MgSO4
- concentrationConcentration
Sources & evidence
- ORD record
- ord-f13c89c6a39a445f93f96a257b6b993a
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05240938
Reaction notes
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