Heptane → (E)-N-(6-Bromochroman-4-ylidene)-2-methylpropane-2-sulfinamide

HRID 1770871Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=O.[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].CCCCCCC>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[N:19][S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Bromochroman-4-one (5.0 g, 22 mmol) and 2-methylpropane-2-sulfinamide (2.6 g, 22 mmol) were dissolved in dry THF (80 mL). Titanium ethoxide (10 g, 44 mmol) was added. The resulting mixture was heated at 60° C. for 2 days. An additional portion of titanium ethoxide (1.0 g, 8.4 mmol) was added after 12 h. The mixture was mixed with heptane and evaporated onto silica gel. Flash chromatography on silica (0-50% EtOAc in heptane) gave the title compound (6.0 g, 83% yield). 1H NMR (500 MHz, CDCl3) δ ppm 1.34 (s, 9H) 3.26-3.32 (m, 1H) 3.47-3.54 (m, 1H) 4.28-4.40 (m, 2H) 6.83 (d, 1H) 7.46 (dd, 1H) 8.06 (d, 1H); MS (ES+) m/z 330 [M+H]+.

Workup

customevaporated onto silica gel

Sources & evidence

ORD record: ord-6a0297ac676e46f894729327b5a14903
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248129B2

Reaction notes

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