Methyl N-(triethylammoniosulfonyl)carbamate → HCID 22612145, compound

HRID 844074Notes

Reaction equation

HRID 844074 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[C:12]([CH:13]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)O)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:12](/[CH:13]=[CH:15]/[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 22612037HCID 22612037, compound

Product 1

HCID 22612145HCID 22612145, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.97 g (2.7 mmol) 2-(4-Fluorophenoxy)-a-[2-(4-methoxyphenyl)ethyl]-3-pyridinemethanol, 0.93 g (3.9 mmol) of Burgess Reagent, and 20 mL of benzene was heated to reflux for 4 h. The cooled mixture was partitioned between 300 mL of EtOAc and 100 mL of saturated aqueous sodium hydrogencarbonate solution, and the separated organic layer was washed with 100 mL of brine, dried (Na2SO4), and evaporated to 1.10 g of an oil. Purification by flash chromatography using 15% EtOAc-hexane as eluant gave 0.39 g (42% yield) of the title compound as an oil. 1H NMR (CDCl3) d 3.60 (2H, d, J=7 Hz), 3.82 (3H, s), 6.48 (1H, dt, J=7, 16 Hz), 6.78 (1H, d, J=16 Hz), 6.86-7.18(9H, m), 7.79 (1H, dd, J=2, 8 Hz), 7.99 (1H, dd, J=2, 5 Hz).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe cooled mixture was partitioned between 300 mL of EtOAc and 100 mL of saturated aqueous sodium hydrogencarbonate solution
  4. washthe separated organic layer was washed with 100 mL of brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to 1.10 g of an oil
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-097eb5c1e65d4d1895fe64d42ce951c4
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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