Methanol → 4-[2-(2-Methoxy-ethoxy)-ethoxy]-2,3-dihydro-1H-isoindole

HRID 424075Notes

Reaction equation

HRID 424075 reaction equation
COC1C=CC(C[N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[CH2:9]2)=CC=1.ClC(OC(Cl)C)=O.CO>ClCCCl>[CH3:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:16][NH:8][CH2:9]2

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 592631462-(4-methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-2,3-dihydro-1H-isoindole

Product 1

HCID 592631354-[2-(2-Methoxy-ethoxy)-ethoxy]-2,3-dihydro-1H-isoindole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-(4-methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-2,3-dihydro-1H-isoindole (45 mg, 0.13 mmol) in 1,2-dichloroethane (2 mL) was treated with α-chloroethyl chloroformate (0.1 mL, 0.93 mmol). After 17 hours, methanol (5 mL) was added and the mixture stirred for 3 hours. The solvents were removed in vacuo to afford the title compound as a greenish-black solid, which was used without further purification. 1H NMR (methanol-d4) 7.36 (1H, t), 6.98 (2H, d), 4.60 (2H, s), 4.57 (2H, s), 4.23-4.21 (2H, m), 3.85-3.83 (2H, m), 3.69-3.67 (2H, m), 3.57-3.54 (2H, m), 3.36 (3H, s). MS: [M+H]+ 238.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-191fb7d055374391bbdc5e86fa8babc4
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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