Sodium Hydroxide → HCID 58026123, compound

HRID 2387334Notes

Reaction equation

HRID 2387334 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:22])([CH3:21])[CH2:11][C:12]([C:17]([F:20])([F:19])[F:18])([OH:16])[CH2:13][C:14]#[CH:15])[C:2]1=2.ClC1C=C(C=CC=1)C(OO)=[O:28].[OH-:34].[Na+]>ClCCl>[O:34]=[S:1]1(=[O:28])[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:22])([CH3:21])[CH2:11][C:12]([C:17]([F:18])([F:19])[F:20])([OH:16])[CH2:13][C:14]#[CH:15])[C:2]1=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 58026175HCID 58026175, compound

Product 1

HCID 58026123HCID 58026123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 150 mg (0.47 mmol) of 6-benzo[b]thiophen-7-yl-6-methyl-4-trifluoromethylhept-1-yn-4-ol in 15 mL of dichloromethane was added 280 mg (˜1.2 mmol) of m-chloroperoxybenzoic acid. After stirring at room temperature for 2.5 hours, the reaction mixture was poured into 30 mL of 1N aqueous NaOH solution and extracted with two 30 mL portions of dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude 6-(1,1-dioxo-1H-1λ6-benzo[b]thiophen-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol was used without further purification.

Workup

  1. extractionextracted with two 30 mL portions of dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude 6-(1,1-dioxo-1H-1λ6-benzo[b]thiophen-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol was used without further purification

Sources & evidence

ORD record
ord-cdc5ecf973ee4cd2b64674c9acd5ee11
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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