Acetyl chloride → N-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)acetamide

HRID 2292486Notes

Reaction equation

HRID 2292486 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1.CN(C1C=CC=CN=1)C.[C:26](Cl)(=[O:28])[CH3:27].CCCCCC>C(Cl)Cl.CCOCC.CCOC(C)=O>[C:13]([C:11]1[C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=[C:2]([NH:1][C:26](=[O:28])[CH3:27])[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 8058HexaneHCID 218852-DimethylaminopyridineHCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 10563380N-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)acetamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-amino-7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]-furan (400 mg, 1.84 mmol) and dimethylaminopyridine (247 mg, 2.024 mmol) in CH2Cl2 (20 mL) is added at 24° C. acetyl chloride (130 μL, 1.84 mmol) in a single portion. The reaction is stirred for 1 h, and monitored by TLC (hexane:EtOAc, 9:1). The mixture is diluted with Et2O (5 mL), and a fine precipitate is filtered off. The filtrate is evaporated to an orange solid which is purified by preparative TLC (hexane:EtOAc, 9:1) to yield N-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)acetamide as a white solid.

Workup

  1. filtrationa fine precipitate is filtered off
  2. customThe filtrate is evaporated to an orange solid which
  3. customis purified by preparative TLC (hexane:EtOAc, 9:1)

Sources & evidence

ORD record
ord-54116ac36a0e43c299e646be354e5f50
Source dataset
uspto-grants-1997_11
Patent number
US05684002

Reaction notes

Loading…