Hexane → N-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]-furan-5-yl)propanamide

HRID 2292485Notes

Reaction equation

HRID 2292485 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:29])[CH2:27][CH3:28].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:29])[CH2:27][CH3:28])[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 8058HexaneHCID 218852-DimethylaminopyridineHCID 62324Propionyl chlorideHCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 21478688N-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]-furan-5-yl)propanamide

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 (61 mg, 0.50 mmol) in CH2Cl2 (5 mL) is added at 24° C. propionyl chloride (160 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)propanamide 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-51a5a9741cbe4017af17b523feb6d4f2
Source dataset
uspto-grants-1997_11
Patent number
US05684002

Reaction notes

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