Acetic Acid → 3,3-Dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuran

HRID 2290135Notes

Reaction equation

HRID 2290135 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[C:16]([O-])(=O)[CH3:17].[Na+].[BH4-].[Na+].[C:23](O)(=O)C>C(O)C.O.CC(C)=O>[CH3:11][C:7]1([CH3:10])[C:6]2[CH:12]=[C:2]([NH:1][CH:16]([CH3:17])[CH3:23])[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]=2[O:9][CH2:8]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 154540815-Amino-3,3-dimethyl-7-isopropyl-2,3-dihydrobenzofuran2×

Product 1

HCID 186991783,3-Dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuranYield 60%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Following general procedure J and using 5-amino-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran (Compound 13, 0.296 g, 1.5 mmol), sodium acetate (0.53 g, 3.9 mmol) and sodium borohydride (1.47 g, 25 mmol) in 5 mL of ethanol, 5 mL of water, 5 mL of acetone (excess) and acetic acid (1.25 mL, 32.74 mmol), the title compound (0.21 g, 60%) was obtained as an oil which was purified by flash column chromatography using 5% ethyl acetate in hexanes as the eluent. 1H NMR (300 MHz, CDCl3): δ 6.30 (d, 1H, J=2.3 Hz), 6.26 (d, 1H, J=2.3 Hz), 4.14 (s, 2H), 3.54 (heptet, 1H, J=6.3 Hz), 3.03 (heptet, 1H, J=7.0 Hz), 1.29 (s, 6H), 1.22 (d, 6H, J=7.0 Hz), 1.19 (d, 6H, J=6.3 Hz).

Sources & evidence

ORD record
ord-5a6bbd05cdbd46179340747e51ad1cee
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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