Triethylamine → HCID 57475771, compound

HRID 2060764Notes

Reaction equation

HRID 2060764 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]([CH2:14][OH:15])[CH2:10][O:11][CH2:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.O>[CH3:23][S:24]([O:15][CH2:14][CH:9]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[CH:13][CH2:12][O:11][CH2:10]1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57475770HCID 57475770, compound

Product 1

HCID 57475771HCID 57475771, compoundYield 115.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of (4-(3-bromophenyl)-3,6-dihydro-2H-pyran-3-yl)methanol (0.305 g, 1.08 mmol) in CH2Cl2 (10 mL) is treated with triethylamine (0.218 g, 2.15 mmol) and then methanesulfonyl chloride (0.148 g, 1.29 mmol) and the reaction is stirred at 0° C. for 30 min. The reaction is diluted with water and extracted with CH2Cl2. The organic layer is dried over Na2SO4 and the solvent is removed under reduced pressure to afford the title compound (0.432 g, 97%). 1H NMR (400 MHz, CDCl3) δ 7.51 (t, J=1.8 Hz, 1H), 7.44-7.41 (m, 1H), 7.31-7.29 (m, 1H), 7.25-7.21 (m, 1H), 6.18 (t, J=2.6 Hz, 1H), 4.33-4.31 (m, 2H), 4.20 (dd, J=1.5, 11.6 Hz, 2H), 4.14-4.08 (m, 1H), 3.72-3.68 (m, 1H), 3.01-2.98 (m, 1H), 2.95 (s, 3H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9231662d218f4adb8c50a4a6326ee5a4
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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