Triethylamine → 4-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-2,6-dichlorophenol

HRID 2199149Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[C:4]([Cl:11])[C:3]=1[OH:12].C(N(CC)CC)C.[Si:20](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:33]([Si:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[O:10][CH2:9][CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([OH:12])=[C:4]([Cl:11])[CH:5]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2,6-dichloro-4-(2-hydroxy-ethyl)-phenol (16) (2.0 g, 9.66 mmol) in methylene chloride (20 mL) at 25° C. was treated with triethylamine (1.35 mL, 9.66 mmol) and tert-butyl diphenylsilylchloride (2.48 mL, 9.66 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with methylene chloride. The organics were washed with a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95:5 petroleum ether/ethyl acetate) afforded 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol (70) (2.60 g, 60%) as a pale yellow oil; HRMS m/e calcd for C24H26Cl2O2Si (M+Na)+ 467.0971, found 467.0977. Exact Mass=444.1079; Molecular Weight=445.47.

Workup

washThe organics were washed with a 1N aqueous hydrochloric acid solution, water
dry with materiala saturated aqueous sodium chloride solution, dried with magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-80655e5b7e5c4994bfd49e5b8ffd50bf
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE046024E1

Reaction notes

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