Ammonium Chloride → HCID 18416682, compound

HRID 990807Notes

Reaction equation

HRID 990807 reaction equation
CON(C)[C:4]([C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=2[S:9][CH:10]=1)=[O:5].[CH3:18][Li].[NH4+].[Cl-]>C1COCC1>[C:4]([C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=2[S:9][CH:10]=1)(=[O:5])[CH3:18]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23392185HCID 23392185, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 18416682HCID 18416682, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-Methoxy-benzo[b]thiophene-3-carboxylic acid methoxy-methyl amide (800 mg, 3.19 mmol) was stirred in dry THF (20 mL) under argon at −78° C. under argon. Methyl lithium (5.0 mL, 1.5 M in hexanes, 2.35 mmol) was added dropwise, and the reaction stirred 1 h at −78° C. and then 1 h while warning to −20° C. The reaction was poured over saturated NH4Cl (40 mL) and extracted with EtOAc (2×30 mL). Organics were washed with brine (25 mL), dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography gave 234 mg (36%) of 3-acetyl-6-methoxy-benzo[b]thiophene as an orange solid. 1H NMR (300 MHz, CDCl3) δ8.64 (d, 1H, J=9.0Hz), 8.11 (s, 1H), 7.30 (d, 1H, J=2.4Hz), 7.10 (dd, 1H, J=9.0, 2.4Hz), 3.89 (s, 3H), 2.63 (s, 3H) (C11H10O2S) C, H. S. Calculated C=64.06, H=4.89, S=15.54; found C=64.31, H=4.82, S=15.50.

Workup

  1. custom1 h
  2. customwhile warning to −20° C
  3. extractionextracted with EtOAc (2×30 mL)
  4. washOrganics were washed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-bf7fdc5d96634a45937bc20d25248969
Source dataset
uspto-grants-2002_10
Patent number
US06462069B2

Reaction notes

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