Benzyl Alcohol → Benzyl 1-(3,4-dichlorobenzyl)-5-formyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate

HRID 1596536

Reaction equation

HRID 1596536 reaction equation
[CH2:1]([OH:8])C1C=CC=CC=1.[H-].[Na+].[H][H].[Cl:13][C:14]1[CH:15]=[C:16]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH2:17][N:18]1[C:26]2[CH2:25][CH2:24][CH2:23][C:22](=[O:27])[C:21]=2[CH:20]=[C:19]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].C(OCC1C=CC=CC=1)=O.Cl>C1COCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH2:17][N:18]1[C:26]2[CH2:25][CH2:24][CH:23]([CH:1]=[O:8])[C:22](=[O:27])[C:21]=2[CH:20]=[C:19]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]

Participants

8

Reactant 6

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 7708Benzyl formateHCID 24758Sodium hydrideHCID 9910428HCID 9910428, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9846845Benzyl 1-(3,4-dichlorobenzyl)-5-formyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylateYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To benzyl alcohol (1.29 g) in dry THF (20 mL) was added sodium hydride (0.48 g) and the reaction was allowed to stir until evolution of hydrogen ceased. Benzyl 1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate (1.28 g) in THF was added, followed by benzyl formate (1.62 g), and the reaction was stirred for a further 2 hours. Upon completion, the reaction was poured into 2M HCl and extracted with ethyl acetate (2×100 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Residual benzyl alcohol was distilled from the oil under reduced pressure to afford an orange gum, which was purified by column chromatography using 20% Ethyl acetate: hexane as eluent to give the title compound as a pale white solid (1.15 g, 84%), NMR d(CDCl3) 2.60 (2H, t), 2.70 (2H, t), 5.20 (2H, s), 5.55 (2H, s), 6.75 (1H, dd), 7.10 (1H, s) 7.20-7.40 (8H, m); M/z (−) 456 (M+).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. distillationResidual benzyl alcohol was distilled from the oil under reduced pressure
  5. customto afford an orange gum, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6bf305ab59b34135933dcb1d9e7fd940
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Linked notes

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