Triethylamine → HCID 23294309, compound

HRID 1955192Notes

Reaction equation

HRID 1955192 reaction equation
S(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][CH:10]=1)(=O)(=O)C.C(O[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39]O)=[CH:33][CH:32]=1)C1C=CC=CC=1.CS([Cl:45])(=O)=O.[CH2:46]([N:48](CC)[CH2:49]C)[CH3:47]>C(Cl)Cl>[ClH:45].[OH:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][N:48]2[CH2:49][CH2:39][CH:38]([CH2:37][C:34]3[CH:33]=[CH:32][CH:31]=[CH:36][CH:35]=3)[CH2:47][CH2:46]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27640763-[4-(Benzyloxy)phenyl]propan-1-olHCID 13079701HCID 13079701, compound

Product 1

HCID 23294309HCID 23294309, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(4-Benzyloxyphenyl)prop-1-yl mesylate. To a solution of 3-(4-benzyloxyphenyl)propan-1-ol (9.76 g, 40 mmol) in 75 mL of methylene dichloride and 7.8 mL of triethylamine was added dropwise methanesulfonyl chloride (9.17 g, 80 mmol) at -20° C. The resulting mixture was allowed to stir at rt for 30 min. and was diluted with 100 mL of methylene dichloride. The solution was washed with 1M HCl (2×100 mL), saturated sodium bicarbonate solution (100 mL) and brine (50 mL), then was dried over MgSO4. Evaporation of solvent gave 12.2 g (95%) of the crude title compound as a white solid. 1H NMR (CDCl3) 2.042 (t, J=6.6 Hz, 2 H), 2.694 (t, J=7.5 Hz, 2 H), 2.984 (s, 3 H), 4.195 (t, J=6.0 Hz, 2 H), 5.045 (s, 2 H), 6.928 (d, J=8.4 Hz, 2 H), 7.116 (d, J=8.4 Hz, 2 H), 7.418 (m, 5 H).

Workup

  1. washThe solution was washed with 1M HCl (2×100 mL), saturated sodium bicarbonate solution (100 mL) and brine (50 mL)
  2. dry with materialwas dried over MgSO4
  3. customEvaporation of solvent

Sources & evidence

ORD record
ord-f0517b813d624d8e9b2cfafd89505fb8
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

Loading…