Acetyl chloride → HCID 59560331, compound

HRID 1643656Notes

Reaction equation

HRID 1643656 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 1N 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 1N 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-0a3afadb1e8c41d1b5592ec702e9cf38
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…