Dimethyl acetylenedicarboxylate → HCID 10639746, compound

HRID 2277129Notes

Reaction equation

HRID 2277129 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[C:14]([O:22][CH3:23])(=[O:21])[C:15]#[C:16][C:17]([O:19][CH3:20])=[O:18]>C1(C)C=CC=CC=1>[C:9]([O:8][C:7]([NH:6][C:2]1[CH:3]=[CH:4][C:5]([OH:1])=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:15]=1[C:14]([O:22][CH3:23])=[O:21])=[O:13])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 317628Tert-butyl n-(2-furyl)carbamate

Product 1

HCID 10639746HCID 10639746, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl furan-2-ylcarbamate C3-2 (55.0 g, 300.2 mmol) and dimethyl but-2-ynedioate (73.5 mL, 600.4 mmol) in toluene (100 mL) was heated at 45° C. for 4 hrs. The solvent was removed in vacuo and the residue was purified by chromatography (silica gel, PE to EA:PE (1:20, v:v)) to give compound C3-2 as a light yellow solid (36.1 g, yield: 37%). 1H NMR (DMSO-d6, 400 MHz) δ: 1.41 (s, 9H), 3.69 (s, 3H), 3.73 (s, 3H), 7.02 (d, J=8.8 Hz, 1H), 7.35 (d, J=9.2 Hz, 1H), 8.93 (s, 1H), 10.07 (s, 1H); MS (ESI+): m/z 238 (M-87).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography (silica gel, PE to EA:PE (1:20, v:v))

Sources & evidence

ORD record
ord-8fa49027861e403a883ad0be9fc8f13c
Source dataset
uspto-grants-2015_09
Patent number
US09133161B2

Reaction notes

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