HCID 22288417, compound → HCID 22288418, compound

HRID 968244Notes

Reaction equation

HRID 968244 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:17]=[C:18]([CH3:20])[CH:19]=1>C(Cl)Cl>[CH:13]([C:14]1[CH:15]=[C:16]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH:17]=[C:18]([CH3:20])[CH:19]=1)=[O:12]

Participants

4

Reactant 2

HCID 22288417HCID 22288417, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22288418HCID 22288418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of PCC (1.36 g, 6.32 mmol) in CH2Cl2 (10 mL) was added a solution of tert-butyl 3-(hydroxymethyl)-5-methylphenylcarbamate (1.0 g, 4.2 mmol) in CH2Cl2 (10 mL) at room temperature. After 18 hours the mixture was filtered through a pad of Celite® and concentrated. Flash column chromatography (15% EtOAc/hexanes) gave tert-butyl 3-formyl-5-methylphenylcarbamate as a white solid. 1H-NM (300 MHz, CDCl3) δ 9.90 (s, 1H), 7.75 (s, 1H), 7.58 (s, 1H), 7.39 (s, 1H), 6.59 (bs, 1H), 2.40 (s, 3H), 1.50 (s, 9H).

Workup

  1. filtrationAfter 18 hours the mixture was filtered through a pad of Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4d3bbe76f37f4a35a4b53c62f2533117
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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