Acetic Acid → HCID 18699171, compound

HRID 2290136Notes

Reaction equation

HRID 2290136 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[C:17]([O-])(=O)[CH3:18].[Na+].[BH4-].[Na+].[C:24](O)(=O)C>C(O)C.O.CC(C)=O>[C:13]([C:4]1[C:5]2[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=2[CH:12]=[C:2]([NH:1][CH:17]([CH3:18])[CH3:24])[CH:3]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran2×

Product 1

HCID 18699171HCID 18699171, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Following general procedure J and using 5-amino-7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran (Compound 14, 0.55 g, 2.5 mmol), sodium acetate (0.85 g, 6.25 mmol) and sodium borohydride (0.76 g, 20 mmol) in 6.5 mL of ethanol, 6.5 mL of water, 5 mL of acetone (excess) and acetic acid (3.15 g, 52.5 mmol), the title compound (0.62 g, 95%) 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 6.40 (d, 1H, J=2.3 Hz), 6.31 (d, 1H, J=2.3 Hz), 4.17 (s, 2H), 3.58 (heptet, 1H, J=6.3 Hz), 3.00-3.25 (br s, 1H), 1.37(s, 9H), 1.33 s, 6H), 1.24 (d, 6H, J=6.2 Hz).

Sources & evidence

ORD record
ord-baae05c6f26044d3ac1d807e04fda459
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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