Triethylamine → HCID 22345528, compound

HRID 584161Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:31]=[CH:30][C:8]([O:9][C:10]([CH3:29])([CH3:28])[C:11](=[O:27])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][CH:15]=2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[CH3:39][S:40]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]([CH3:29])([CH3:28])[C:11](=[O:27])[CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[CH:18][CH:19]=2)=[CH:30][CH:31]=1)(=[O:42])=[O:41]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-[4-(3-hydroxypropyl)phenoxy]-1-[4-(tert-butoxycarbonyl)phenoxy]-3-methyl-2-butanone (0.312 g, 0.73 mmol) in dry dichloromethane (15 ml) was cooled to 0-5° C. and treated with triethylamine (0.23 ml, 1.65 mmol) followed with methanesulfonyl chloride (0.10 ml, 1.29 mmol) added dropwise over 2 minutes. The reaction mixture was stirred at 0° C. for 45 minutes and then quenched by the addition of ethyl acetate and water. The organic phase was washed with brine, dried (magnesium sulfate) and concentrated. The residue was chromatographed on silica gel (elution toluene-ethyl acetate, 85:15) to give 0.369 g (100%) of the title material as a clear oil.

Workup

additionadded dropwise over 2 minutes
customquenched by the addition of ethyl acetate and water
washThe organic phase was washed with brine
dry with materialdried (magnesium sulfate)
concentrationconcentrated
customThe residue was chromatographed on silica gel (elution toluene-ethyl acetate, 85:15)

Sources & evidence

ORD record: ord-0b5a73b36b514689b41fffd05894f6c8
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924391B2

Reaction notes

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