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

HRID 1493048Notes

Reaction equation

HRID 1493048 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 (100g, 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-f7b30947f53d4eac9153d1f7eb484f95
Source dataset
uspto-grants-1994_12
Patent number
US05376681

Reaction notes

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