HCID 70937102, compound → HCID 86761670, compound

HRID 1875260Notes

Reaction equation

HRID 1875260 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([S:17]([NH:20][CH3:21])(=[O:19])=[O:18])[N:5]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[CH2:7][OH:8]>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[N:3]=[C:4]([S:17]([NH:20][CH3:21])(=[O:19])=[O:18])[N:5]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:14])[CH3:15])[C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 70937102HCID 70937102, compound

Product 1

HCID 86761670HCID 86761670, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of the above alcohol, MnO2 (0.42 g, 4.86 mmol) in CH2Cl2 (5 mL) was stirred at RT for 1 h. Additional MnO2 (0.42 g, 4.86 mmol) was added and the reaction mixture was heated at 40° C. overnight and then evaporated and purified by silica gel chromatography (0-35% EtOAc/hex) to afford the title compound (0.083 g, 48%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.93 (s, 1H), 6.00 (s, 2H), 5.33 (br. s., 1H), 3.60-3.69 (m, 2H), 2.90 (s, 3H), −0.02 (s, 9H).

Workup

  1. customevaporated
  2. custompurified by silica gel chromatography (0-35% EtOAc/hex)

Sources & evidence

ORD record
ord-c3010c89c2554f218147715ed63b602b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…