Methanesulfonyl chloride → HCID 178505320, compound

HRID 45003Notes

Reaction equation

HRID 45003 reaction equation
[C:1]([O:20][CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)(Cl)Cl>[CH3:29][S:30]([O:28][C@H:25]1[CH2:26][CH2:27][C@H:22]([CH2:21][O:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:23][CH2:24]1)(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178521567HCID 178521567, compound

Product 1

HCID 178505320HCID 178505320, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

trans-4-[(Trityloxy)methyl]cyclohexanol (2.72 g, 0.00730 mol) was dissolved in chloroform (30.0 mL) and the mixture was cooled at 0° C. To this mixture was added TEA (1.4 mL, 0.010 mol) and methanesulfonyl chloride (0.68 mL, 0.0088 mol) and the resulting mixture was stirred at 0° C. for 2 hours The reaction was then extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and the concentrated in vacuo. 1H NMR (CDCl3): δ 7.43 (m, 6H), 7.20-7.31 (m, 9H), 4.57 (m, 1H), 3.00 (m, 3H), 2.90 (m, 2H), 2.16 (m, 2H), 1.93 (m, 2H), 1.09-1.60 (m, 5H).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic extracts were washed with water, saturated NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationthe concentrated in vacuo

Sources & evidence

ORD record
ord-7d1dd23f08954eb6be4503b790e49179
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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