Acetyl chloride → HCID 59560331, compound

HRID 1177182Notes

Reaction equation

HRID 1177182 reaction equation
CCN(CC)CC.[C:8](Cl)(=[O:10])[CH3:9].[CH3:12][O:13][C:14]([C:16]1[CH:26]=[C:25]([O:27][CH:28]2[CH2:31][NH:30][CH2:29]2)[C:19]2[CH2:20][C:21]([CH3:24])([CH3:23])[O:22][C:18]=2[CH:17]=1)=[O:15]>C(Cl)Cl>[CH3:12][O:13][C:14]([C:16]1[CH:26]=[C:25]([O:27][CH:28]2[CH2:29][N:30]([C:8](=[O:10])[CH3:9])[CH2:31]2)[C:19]2[CH2:20][C:21]([CH3:24])([CH3:23])[O:22][C:18]=2[CH:17]=1)=[O:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59559971HCID 59559971, compound

Product 1

HCID 59560331HCID 59560331, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (400 uL, 2.87 mmol) and acetyl chloride (70 uL, 0.99 mmol) were added to a solution of 4-(azetidin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (193c) (300 mg, 0.96 mmol) in CH2Cl2 (15 mL). The mixture was stirred at room temperature for 4 hr, then quenched with 1 N aqueous HCl (80 mL), and extracted with CH2Cl2 (80 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 80% EtOAc in hexanes to give a colorless oil (239 mg, 73% yield). 1H NMR (400 MHz, CDCl3) δ 7.12 (br. s., 1 H) 6.76 (br. s., 1 H) 5.03 (br. s., 1 H) 4.55 (br. s., 1 H) 4.43 (br. s., 1 H) 4.03-4.19 (m, 2 H) 3.89 (s, 3 H) 3.00 (s, 2 H) 1.92 (s, 3 H) 1.51 (br. s., 6 H).

Workup

  1. customquenched with 1 N aqueous HCl (80 mL)
  2. extractionextracted with CH2Cl2 (80 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatograph
  6. washeluting with 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-0576ecf52b08402ab8f1c3af998fc4ad
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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