Triphenylphosphine → HCID 67360431, compound

HRID 1804791Notes

Reaction equation

HRID 1804791 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]2[C:13]([CH:14]=1)=[C:12]([OH:15])[CH:11]=[CH:10][CH:9]=2)=[O:5].[CH2:23]([O:25][C:26]1[CH:36]=[CH:35][C:29]2[C:30]([CH2:33]O)=[CH:31][O:32][C:28]=2[CH:27]=1)[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O>C1COCC1>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:33][C:30]1[C:29]3[CH:35]=[CH:36][C:26]([O:25][CH2:23][CH3:24])=[CH:27][C:28]=3[O:32][CH:31]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 596001381-tert-butyl 2-ethyl 4-hydroxy-1H-indole-1,2-dicarboxylateHCID 67360905(6-Ethoxy-benzofuran-3-yl)-methanolHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 67360431HCID 67360431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Hydroxy-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (2) (5.2 g, 17.2 mmol), (6-ethoxy-benzofuran-3-yl)-methanol (28a) (3.3 g, 17.2 mmol) and triphenylphosphine (5.4 g, 20.6 mmol) are dissolved in 30 ml of THF and cooled to 0° C. Then 40% ethyl azodicarboxylate solution in THF (9 ml, 20.6 mmol) is added drop wise. After completed addition the mixture is stirred for 16 h (TLC control) at rt. Then the mixture is evaporated under reduced pressure. The residue is diluted with ethyl acetate, washed sat. NaHCO3- and NaCl-solution, and dried over Na2SO4. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel).

Workup

  1. additionaddition the mixture
  2. customThen the mixture is evaporated under reduced pressure
  3. additionThe residue is diluted with ethyl acetate
  4. washwashed sat. NaHCO3- and NaCl-solution
  5. dry with materialdried over Na2SO4
  6. customThe crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel)

Sources & evidence

ORD record
ord-e7620c80298640a6b7c1738c026a5800
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

Loading…