Water → HCID 68770274, compound

HRID 1947486Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11](F)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20](=[O:23])[CH2:21][SH:22].CCN(CC)CC.O>CS(C)=O>[CH3:18][O:19][C:20]([C:21]1[S:22][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:16]=[CH:15][C:12]=2[CH:13]=1)=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-benzyloxy-2-fluoro-benzaldehyde (1.3 g, 5.6 mmol) in DMSO (55 mL) was added mercapto-acetic acid methyl ester (1.2 mL, 11.3 mmol) and Et3N (2.4 mL, 1.7 g, 16.8 mmol) and the reaction mixture was heated (80° C., 12 h). The reaction mixture was cooled (rt), treated with H2O (100 mL) and filtered. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-30%) to provide the title compound as yellow solid (1.6 g, 96%). MS (ESI): mass calcd. for C17H14O3S, 298.1; m/z found, 299.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.98 (s, 1H), 7.75 (d, J=8.8, 1H), 7.53-7.30 (m, 6H), 7.10 (dd, J=8.8, 2.3, 1H), 5.14 (s, 2H), 3.92 (s, 3H).

Workup

temperatureThe reaction mixture was cooled (rt)
filtrationfiltered
customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-8f0c8ffa686644709134961ef7a4996b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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