5-Allyloxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester → 5-Hydroxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester

HRID 434018Notes

Reaction equation

HRID 434018 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][CH2:20][C:21]2[CH:25]=[CH:24][S:23][CH:22]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]CC=C)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCCl.N1CCOCC1.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][CH2:20][C:21]2[CH:25]=[CH:24][S:23][CH:22]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 120944655-Allyloxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester

Product 1

HCID 120944625-Hydroxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl esterYield 108.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 18756449Dichloromethane morpholine waterSolvent

Procedure

To 5-allyloxy-1-[(2-thiophen-3-yl)ethyl]-1H-indole-2-carboxylic acid ethyl ester (1.36 g, 3.8 mmol) was added a mixture of dichloromethane:morpholine:water (100:10:2, 50 mL) followed by the addition of tetrakis(triphenylphosphine) palladium (0) (300 mg). After stilling at room temperature for 18 h, the reaction was partitioned between dichloromethane and water. The organic layer was washed with HCl (3N), NaHCO3, brine and dried over Na2SO4. Purification by flash column chromatography (silica gel, 10-30% EtOAc/hexanes) yielded the desired product as a off-white solid (1.3 g, 86%).

Workup

  1. customthe reaction was partitioned between dichloromethane and water
  2. washThe organic layer was washed with HCl (3N), NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. customPurification by flash column chromatography (silica gel, 10-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b90100b1a1374342bc64ac8a774486ba
Source dataset
uspto-grants-2003_12
Patent number
US06670388B1

Reaction notes

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