2-Propanol, 1-methoxy-2-methyl- → 1-Methoxy-2-methylpropan-2-yl 4-nitrophenyl carbonate

HRID 876897Notes

Reaction equation

HRID 876897 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH3:7])([OH:6])[CH3:5].Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:10]>>[C:9](=[O:10])([O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)[O:6][C:4]([CH3:7])([CH3:5])[CH2:3][O:2][CH3:1]

Participants

3

Reactant 2

HCID 771372-Propanol, 1-methoxy-2-methyl-HCID 821294-Nitrophenyl chloroformate

Product 1

HCID 577857091-Methoxy-2-methylpropan-2-yl 4-nitrophenyl carbonateYield 87%

Procedure

1-Methoxy-2-methyl-2-propanol (3.50 ml, 30 mmol) was treated with 4-nitrophenyl chloroformate according to conditions similar to the ones described above with respect to Intermediate 2, Step 2 to provide, after purification by column chromatography over silica gel (eluting with Hexanes/EtOAc 99:1 to 70:30), 1-methoxy-2-methylpropan-2-yl 4-nitrophenyl carbonate (7.02 g, 87% yield) as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 8.26 (d, J=9.2 Hz, 2H), 7.36 (d, J=9.2 Hz, 2H), 3.56 (s, 3H), 3.43 (s, 3H), 1.57 (s, 6H).

Workup

  1. customto provide

Sources & evidence

ORD record
ord-d210160a19e6441f93442a609ad3359e
Source dataset
uspto-grants-2015_03
Patent number
US08987195B2

Reaction notes

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