Phenol → 1,1-Dimethylethyl [1,1-dimethyl-2-(phenyloxy)ethyl]carbamate

HRID 852625Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CS(O[CH2:15][C:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:18])[CH3:17])(=O)=O>CN(C=O)C>[CH3:18][C:16]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:15])[CH2:17][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of phenol (2.1 g, 22.4 mmol, 3 equiv) in DMF (10 ml) at room temperature were added NaH (60% dispersion in mineral oil, 360 mg, 9.0 mmol, 1.2 equiv) and after 10 min 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-methylpropyl methanesulfonate (D273) (2 g, 7.5 mmol, 1 equiv) and the resulting solution was stirred at 50° C. for 2 h then cooled to room temperature and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 9/1 to 6/1) gave 1,1-dimethylethyl [1,1-dimethyl-2-(phenyloxy)ethyl]carbamate (D274) (180 mg, 9%) as a yellow oil.

Workup

temperaturethen cooled to room temperature
concentrationconcentrated in vacuo
customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 9/1 to 6/1)

Sources & evidence

ORD record: ord-e39cd99a89b1427b832e951269e81c96
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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