1,4-Butanediol → HCID 67173814, compound

HRID 1916988Notes

Reaction equation

HRID 1916988 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:27])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH3:19])=[CH:4][CH:3]=1.[CH2:28](O)[CH2:29][CH2:30][CH2:31][OH:32]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH:18]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH3:19])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80641,4-ButanediolHCID 67415262HCID 67415262, compound

Product 1

HCID 67173814HCID 67173814, compoundYield 51%

Procedure

The named compound was synthesised from 3-(4-chlorophenyl)-2-[1-(4-chlorophenyl)-ethyl]-3-hydroxy-2,3-dihydroisoindol-1-one (498 mg, 1.37 mmol, 1 equiv.) and 1,4-butanediol (616 mg, 6.85 mmol, 5 equiv.) using General Procedure A and obtained as a pale yellow oil (242 mg, 51%). 1H NMR (300 MHz, CDCl3): 7.87-7.83 (m, 1H, C(O)═C═CH), 7.53-7.46 (m, 2H, Ar—H), 7.07-7.03 (m, 9H, Ar—H), 4.41 (q, J=7.2 Hz, 1H, N—CH), 3.70 (m, 2H, HO—CH2), 3.29-3.25 and 3.01-2.95 (m, 2H, OCH2), 1.86 (d, J=7.2 Hz, 3H, CH3), 1.77-1.68 (m, 4H, CH2). 13C NMR (75 MHz, CDCl3): 168.31, 145.26, 141.47, 137.76, 134.79, 133.15, 133.06, 132.84, 130.20, 129.67, 128.75, 128.41, 128.27, 123.71, 123.27, 95.44, 63.35, 62.89, 52.49, 29.96, 26.48, 20.08. m/z (ES): 470 [M+H]+. HPLC: Rt=3.76 min. Anal.: calc. for C26H25Cl2NO3: C, 66.39; H, 5.36; N, 2.98. Found: C, 66.33; H, 5.25; N, 2.46.

Sources & evidence

ORD record
ord-ce0ca29f71994a44a91bf9e4e19873b0
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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