Water → 5-Acetylamino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran

HRID 964796Notes

Reaction equation

HRID 964796 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:7]([CH3:19])=[C:8]([CH3:18])[C:9]2[O:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10]=2[C:16]=1[CH3:17].C(N(CC)CC)C.O>O1CCCC1>[C:1]([NH:5][C:6]1[C:7]([CH3:19])=[C:8]([CH3:18])[C:9]2[O:13][C:12]([CH3:14])([CH3:15])[CH2:11][C:10]=2[C:16]=1[CH3:17])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 100358625-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran

Product 1

HCID 107768875-Acetylamino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuranYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (460 mg, 5.84 mmol) was added dropwise with ice cooling to a solution of 5-amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran (100 g, 4.87 mmol) and triethylamine (640 mg, 6.33 mmol) in tetrahydrofuran (20 ml). After the addition was completed, the mixture was stirred for 4 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with saturated sodium bicarbonate solution and saturated saline, dried and concentrated. The residue was purified by column chromatography on silica gel (chloroform-methanol, 97:3) to obtain the desired compound (920 mg, yield: 76.4%). A part of it was recrystallized from dichloromethane-isopropyl ether, m.p. 190° C. (dichloromethane-isopropyl ether).

Workup

  1. additionAfter the addition
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with saturated sodium bicarbonate solution and saturated saline
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (chloroform-methanol, 97:3)

Sources & evidence

ORD record
ord-4b44ac7530e74faaa83bb5650987f980
Source dataset
uspto-grants-1998_06
Patent number
US05770772

Reaction notes

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