Water → HCID 178505331, compound

HRID 2306602Notes

Reaction equation

HRID 2306602 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C@@H:14]1[CH2:17][C@H:16]([OH:18])[CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.O>ClCCl>[CH2:6]([O:13][C@@H:14]1[CH2:17][C@H:16]([O:18][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178521639HCID 178521639, compound

Product 1

HCID 178505331HCID 178505331, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.44 ml, 5.7 mmol) was added dropwise to a stirred solution of cis-3-benzyloxy-1-hydroxycyclobutane (0.85 g, 4.77 mmol) and triethylamine (1.0 ml, 7.2 mmol) in dry dichloromethane (15 ml) at 0° C. under nitrogen. The white suspension was stirred at 0° C. for 1.5 h then poured into water (50 ml) and extracted with dichloromethane (2×30 ml). The extracts were dried (Na2SO4), filtered and concentrated. The oil was filtered through a plug of silica gel, eluting with ethyl acetate, to give cis-3-benzyloxy-1-methanesulfonyloxycyclobutane (1.27 g, 100%) as a yellow oil; 1H NMR (250 MHz, CDCl3) δ 2.26-2.39 (2H, m), 2.77-2.91 (2H, m), 2.97 (3H, s), 3.74 (1H, qn, J=7 Hz), 4.42 (2H, s), 4.68 (1H, qn, J=7 Hz), 7.26-7.42 (5H, m).

Workup

  1. extractionextracted with dichloromethane (2×30 ml)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationThe oil was filtered through a plug of silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f7f6488596cf497381bf7786e35e11ec
Source dataset
uspto-grants-2004_12
Patent number
US06828322B2

Reaction notes

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