Triethylamine → 3-(2,6-Dimethylbenzyloxy)-2-methoxybenzyl methanesulfonate

HRID 337270Notes

Reaction equation

HRID 337270 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([O:14][CH3:15])=[C:8]([CH2:12][OH:13])[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:28][S:29]([O:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]2[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:2]=2[CH3:1])[C:7]=1[O:14][CH3:15])(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66959407HCID 66959407, compound

Product 1

HCID 866570093-(2,6-Dimethylbenzyloxy)-2-methoxybenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-(2,6-dimethylbenzyloxy)-2-methoxyphenyl)methanol (Step B, 9.5 g, 32.7 mmol) and triethylamine (5.80 g, 57.4 mmol) in dry CH2Cl2 (100 ml) was added drop wise methanesulfonyl chloride (3.5 ml, 45 mmol) at 0° C. under argon. The reaction mixture was warmed to room temperature for 6 hours or until all the starting material is consumed, neutralized with cooled 10% Na2CO3 and extracted with CH2Cl2. The organic layer was concentrated, and purified by flash chromatography on a silica gel column (hex: methylene chloride 2:1) to give the title compound as light yellow oil

Workup

  1. customis consumed
  2. temperaturewith cooled 10% Na2CO3
  3. extractionextracted with CH2Cl2
  4. concentrationThe organic layer was concentrated
  5. custompurified by flash chromatography on a silica gel column (hex: methylene chloride 2:1)

Sources & evidence

ORD record
ord-5efbc75b3aa648ffbfa85a2cc98cc9a5
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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