Methyl chloroformate → 4-(tert-Butyl)-2-(2-cyanopropan-2-yl)phenyl methyl carbonate

HRID 76784Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:27]([O:29][CH3:30])=[O:28]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:27](=[O:28])([O:29][CH3:30])[O:16][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][C:9]=1[C:11]([C:12]#[N:13])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred mixture of compound 15 (126.6 g, 0.564 mol), DMAP (6.0 g) and DIEA (188 g, 1.46 mol) in anhydrous DCM (1500 mL) was added dropwise methyl chloroformate (110 g, 1.17 mol) in anhydrous DCM (300 mL) at 0° C. within 2 hours. After stirring for 12 hours at 0° C., ice-water (1.5 L) was added and the mixture was stirred at 0° C. for 30 minutes. The organic layer was separated and washed with 1N HCl, water, and brine. The DCM solution was dried over MgSO4 and concentrated in vacuo to give compound 16 as a yellow solid. 1H NMR (DMSO-d6; 400 MHz) δ 7.47 (m), δ 7.39 (d), δ 7.24 (d), δ 3.84 (s), δ 1.71 (s), δ 1.30 (s).

Workup

stirringthe mixture was stirred at 0° C. for 30 minutes
customThe organic layer was separated
washwashed with 1N HCl, water, and brine
dry with materialThe DCM solution was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a5886865add44bc59dbaf8e5cadf1497
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835639B2

Reaction notes

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