(Diethylamino)sulfur trifluoride → HCID 59305343, compound

HRID 2240959Notes

Reaction equation

HRID 2240959 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:18]3[CH2:21][CH:20](O)[CH2:19]3)[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1.C(N(S(F)(F)[F:30])CC)C>ClCCl>[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:18]([F:30])[CH2:19][CH:20]=[CH2:21])[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59305304HCID 59305304, compound

Product 1

HCID 59305343HCID 59305343, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(4-Difluoromethoxy-phenylethynyl)-phenyl]-cyclobutanol (0.820 gm, 2.61 mmol) was dissolved in dichloromethane (10 ml) and treated with (diethylamino)sulfur trifluoride (DAST, 0.500 gm, 3.20 mmol). Upon completion of reaction as determined by thin layer chromatography (TLC) the crude material was absorbed onto silica and purified by column chromatography (gradient elution; 0%-10% EtOAc in hexanes) to yield an oil 267 mg (32%); 1H NMR (500 MHz, DMSO-d6) δ ppm 2.55-2.75 (m, 2H) 4.97-5.20 (m, 2H) 5.52-5.83 (m, 2H) 7.04-7.32 (m, 3H) 7.40-7.48 (m, 2H) 7.50-7.55 (m, 2H) 7.62 (d, J=8.8 Hz, 2H); MS (EI) m/z 316 [M+·].

Workup

  1. customUpon completion of reaction
  2. customwas absorbed onto silica
  3. custompurified by column chromatography (gradient elution; 0%-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c7aad93caf8b4b118b419c0047dd73f3
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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