Sodium Chloride → {1-[(Benzyloxy)methyl]cyclobutyl}methyl methanesulfonate

HRID 1180764Notes

Reaction equation

HRID 1180764 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].[Cl-].[Na+]>ClCCl>[CH3:23][S:24]([O:15][CH2:14][C:10]1([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11][CH2:12][CH2:13]1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11458402(1-((Benzyloxy)methyl)cyclobutyl)methanol

Product 1

HCID 11346646{1-[(Benzyloxy)methyl]cyclobutyl}methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 12.0 g (59.0 mmol) of {1-[(benzyloxy)methyl]cyclobutyl}methanol in 180 mL of dichloromethane was added 9.93 ml (70.8 mmol) of triethylamine at 0° C. followed by the addition of 5.02 mL (64.9 mmol) of methanesulfonyl chloride. After stirring for 2 h, saturated sodium chloride solution was added. The organic phase was isolated, dried using magnesium sulfate, and concentrated under vacuum to afford the crude product, which was used directly in the next step. 1H NMR (300 MHz, CDCl3) δ 7.39-7.32 (m, 5H), 4.57 (s, 2H), 4.30 (s, 2H), 3.52 (s, 2H), 2.98 (s, 3H), 1.95 (m, 6H).

Workup

  1. customThe organic phase was isolated
  2. customdried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-14527ff28ba54ae0a76ac68d373da9ec
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

Loading…