Tetrahydrofuran → HCID 66764989, compound

HRID 1466787Notes

Reaction equation

HRID 1466787 reaction equation
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])[CH3:3].[H-].[Na+].[CH2:14]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([Cl:30])[CH:28]=2)[C:23]([S:31][C:32]2[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=2)C=O)=[C:22]1[CH3:40])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:41]1COCC1>CCOC(C)=O>[CH3:41][O:6][C:4](=[O:5])/[CH:2]=[CH:3]/[C:34]1[CH:37]=[CH:38][CH:39]=[C:32]([S:31][C:23]2[C:24]3[C:29](=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[N:21]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:22]=2[CH3:40])[CH:33]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 53413272TrimethylphosphonoacetateHCID 86686481HCID 86686481, compound

Product 1

HCID 66764989HCID 66764989, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Trimethylphosphonoacetate (248 μL, 1.72 mmol) was dissolved in THF (10 mL) and the reaction was cooled to 0° C. then sodium hydride (60% dispersion in mineral oil, 0.042 g, 1.77 mmol) was added and the reaction stirred for 10 minutes. 3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzaldehyde (0.225 g, 0.57 mmol) as a THF solution was added and the reaction was allowed to warm to room temperature. After 30 minutes, the reaction was diluted with EtOAc then quenched with aq. HCl (5 mL, 1M). Standard workup procedure afforded the title compound.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 30 minutes
  3. customthen quenched with aq. HCl (5 mL, 1M)

Sources & evidence

ORD record
ord-a24bddee749f43fbb5aaafe371a63505
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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