tert-Butyl (4-(hydroxymethyl)-2-methoxyphenyl)carbamate → Tert-butyl 4-formyl-2-methoxyphenylcarbamate

HRID 576453Notes

Reaction equation

HRID 576453 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([O:28][CH3:29])[CH:15]=1>ClCCl>[CH:13]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[C:16]([O:28][CH3:29])[CH:15]=1)=[O:12]

Participants

4

Reactant 2

HCID 86720230tert-Butyl (4-(hydroxymethyl)-2-methoxyphenyl)carbamateHCID 178418287HCID 178418287, compound

Product 1

HCID 84804049Tert-butyl 4-formyl-2-methoxyphenylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of finely ground PCC (80 mg, 0.56 mmol) and Celite (80 mg) in dry dichloromethane (2 ml) at room temperature was added drop wise a solution of the alcohol 8 (92.9 mg, 0.37 mmol) in dichloromethane (1 ml followed by 0.7 ml rinse). The mixture was stirred in the dark for 20 minutes. The reaction mixture was adsorbed on silica gel and purified by normal phase MPLC, eluting with hexanes/ethyl acetate 20-40% gradient. GC-MS EI+: m/z 251 (M+); LC-MS ESI+: m/z 252 (M+H+). Yield: 72.7 mg (78%). H-NMR (400 MHz, CD2Cl2): 9.06 (1H, brs) 8.02 (1H, d, J=8 Hz) 7.65 (1H, s) 6.92 (1H, dd, J=8 Hz, 0.4 Hz) 4.67 (1H, s) 1.22 (9H, s).

Workup

  1. custompurified by normal phase MPLC
  2. washeluting with hexanes/ethyl acetate 20-40% gradient

Sources & evidence

ORD record
ord-b6a636dd844742e7b27d4da0ec17a08a
Source dataset
uspto-grants-2015_05
Patent number
US09040019B2

Reaction notes

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