Methanol → HCID 70855548, compound

HRID 591037Notes

Reaction equation

HRID 591037 reaction equation
C(Cl)(=[O:3])C.[Br:5][C:6]1[C:7]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:8]=2[S:9][C:10]=1[CH:11]([O:14][Si](C)(C)C)C#N.[CH3:24][OH:25]>>[Br:5][C:6]1[C:7]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:8]=2[S:9][C:10]=1[CH:11]([OH:14])[C:24]([OH:3])=[O:25]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 6367Acetyl chlorideHCID 70855546HCID 70855546, compound

Product 1

HCID 70855548HCID 70855548, compoundYield 74%

Procedure

Acetyl chloride (2.6 mL, 36.3 mmol) was dropped at 0° C. in methanol (20 mL). After minutes, a solution of (3-bromo-4-methyl-benzo[b]thiophen-2-yl)-trimethylsilanyloxy-acetonitrile (428 mg, 1.21 mmol) in methanol (5 mL) was added at 0° C. to the reaction. The mixture was warmed at room temperature for 2 hours and then concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL). The organic layer was washed with an aqueous solution of sodium hydroxyde 1M for 2 hours and was then acidified to pH 2 with an hydrochloric acid solution 1N. The organic layer was washed with brine (20 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure to afford the desired acid (23g) as a white solid (270 mg, 0.9 mmol, 74%) without further purification.

Workup

  1. waitAfter minutes
  2. concentrationconcentrated under vacuum
  3. additionThe residue was diluted with ethyl acetate (30 mL)
  4. washThe organic layer was washed with an aqueous solution of sodium hydroxyde 1M for 2 hours
  5. washThe organic layer was washed with brine (20 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-38273233113c460fb64d177da22760b9
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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