Acetyl chloride → HCID 22143532, compound

HRID 985195Notes

Reaction equation

HRID 985195 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].CCN(CC)CC.[OH:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([CH3:21])[S:18][C:17]=2[CH:22]=1>C1COCC1.CCOC(C)=O>[C:1]([O:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([CH3:21])[S:18][C:17]=2[CH:22]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 122034952-Methyl-1-benzothiophen-6-OL

Product 1

HCID 22143532HCID 22143532, compoundYield 126.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetyl chloride (1.5 ml, 1.66 g, 21 mmole) and Et3N (3 ml, 2.18 g, 21.5 mmole) were added, sequentially, to a solution of 6-hydroxy-2-methylbenzo[b] thiophene 8a (2.51 g, 15 mmole) in THF (120 ml) at 0°. The reaction was left stirring for 14 hours, gradually warming to ambient temperature, then diluted with EtOAc (100 ml) and washed with H2O (100 ml) and brine (100 ml). The combined aqueous layers were extracted with EtOAc (100 ml). The combined organic extracts were subsequently dried over Na2SO4 and concentrated, in vacuo, to give 3.9 g of a yellow solid which was purified by silica gel chromatography. Elution with hexane: Et2O (90:10) and evaporation of the appropriate fractions gave 2.93 g (93%) of a white solid. 1H NMR (DMSO-d6) δ7.70 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=2.2 Hz), 7.12 (1H, s), 7.07 (1H, dd, J=2.2, 8.6 Hz), 2.54 (3H, s), 2.27 (3H, s). Anal Calcd. for C11H10O2S: C, 64.05; H, 4.89; S, 15.55. Found: C, 63.84; H, 4.93; S, 15.57.

Workup

  1. customat 0°
  2. waitThe reaction was left
  3. washwashed with H2O (100 ml) and brine (100 ml)
  4. extractionThe combined aqueous layers were extracted with EtOAc (100 ml)
  5. dry with materialThe combined organic extracts were subsequently dried over Na2SO4
  6. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-ac36cef9815f4d20a87ee91a614982f3
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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