Methyl iodide → 7-t-Butyl-5-[ethyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

HRID 2290154Notes

Reaction equation

HRID 2290154 reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:6]=1[CH3:25])([CH3:4])([CH3:3])[CH3:2].[CH2:26]([Li])[CH2:27]CC.IC>O1CCCC1>[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N:16]([CH2:26][CH3:27])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:6]=1[CH3:25])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 186991917-t-Butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran2×HCID 178418339Butyllithium

Product 1

HCID 186991837-t-Butyl-5-[ethyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuranYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure L and using 7-t-butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 53), (0.12 g, 0.35 mmol), 1.6M solution of n-butyllithium in hexanes (0.442 mL, 0.7 mmol) and iodomethane (0.281 mL, 3.5 mmol) in 2 mL of anhydrous tetrahydrofuran, the title compound (0.11 9 g, 92%) was obtained as a brown oil. 1H NMR (300 MHz, CDCl3): δ 6.76 (d, 2H, J=9.0 Hz), 6.72 (s, 1H), 6.41 (d, 2H, J=9.0 Hz), 4.14 (s, 2H), 3.73 (s, 3H), 2.60 (s, 3H), 1.52 (s, 9H), 1.26 (s, 6H), 1.20 (t, 3H, J=7.1 Hz).

Sources & evidence

ORD record
ord-61afa156130c421ba62b4e8bd0d57de8
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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