Diethyl Ether → Methyl 2-(3-(3-(diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-oxopropyl)benzoate

HRID 258480Notes

Reaction equation

[C:1]1([Si:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:29]([CH3:32])([CH3:31])[CH3:30])[O:8][C:9]2[CH:10]=[C:11]([CH:15]([OH:28])[CH2:16][CH2:17][C:18]3[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CCOCC>C(Cl)Cl>[C:33]1([Si:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:29]([CH3:30])([CH3:31])[CH3:32])[O:8][C:9]2[CH:10]=[C:11]([C:15](=[O:28])[CH2:16][CH2:17][C:18]3[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:12]=[CH:13][CH:14]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The alcohol of Step 1 (93 g, 0.179 mol), dissolved in CH2Cl2 (300 mL) was added to a mixture of 4A molecular sieve (94 g, milled) and PCC, (pyridinium chlorochromate, 69 g, 0.321 mol) in CH2Cl2 (1 L) at 10° C. The mixture was then allowed to warm to 20° C. for 2 h and ether (1 L) was introduced. The mixture was filtered through silica and was washed with ether (2 L) and EtOAc:hexane 1:1 (1 L). Evaporation of the filtrate and flash chromatography (10% EtOAc:hexane) of the crude mixture on silica gave the title product. Yield: 81 g, 87%.

Workup

filtrationThe mixture was filtered through silica
washwas washed with ether (2 L) and EtOAc:hexane 1:1 (1 L)
customEvaporation of the filtrate and flash chromatography (10% EtOAc:hexane) of the crude mixture on silica

Sources & evidence

ORD record: ord-c581176613184b319a4cc74f019ce24f
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266568

Reaction notes

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