Methanol → Tert-butyl 4-((methoxycarbonyl)methyl)benzoate

HRID 1919915Notes

Reaction equation

HRID 1919915 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18]CN=C=NCCCN(C)C.CO>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:18][O:16][C:15](=[O:17])[CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 598545182-(4-(Tert-butoxycarbonyl)phenyl)acetic acid

Product 1

HCID 57611856Tert-butyl 4-((methoxycarbonyl)methyl)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

[4-(tert-Butoxycarbonyl)phenyl]acetic acid (2.94 g, 12.4 mmol) and DMAP (152 mg, 1.24 mmol) were dissolved in CH2Cl2 (50 mL) and cooled to 0° C. EDCI (3.10 g, 16.2 mmol) and MeOH (660 μL, 16.2 mmol) were added. After stirring for 30 min at 0° C., the reaction was allowed to warm to room temperature and stirred 2 h. The mixture was then diluted with CH2Cl2, washed (sat. NaHCO3, brine), dried (MgSO4), and concentrated. Flash chromatography on silica gel (0-10% EtOAc/hexanes) afforded tert-butyl 4-(2-methoxy-2-oxoethyl)benzoate as a colorless oil. 1H NMR (CDCl3) δ 7.93 (d, J=8.2 Hz, 2H), 7.31 (d, J=8.5 Hz, 2H), 3.68 (s, 3H), 3.66 (s, 2H), 1.57 (s, 9H). MS (ESI) calcd [M+Na]+ 273.1, found 273.1.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred 2 h
  3. washwashed (sat. NaHCO3, brine)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-841c495e15ff435b86acb5ca741c299a
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

Loading…