Methanesulfonyl chloride → 1-Hexadecyloxy-2-methanesulfonyloxymethyl-3-triphenylmethoxypropane

HRID 34301Notes

Reaction equation

HRID 34301 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:22][CH2:23][CH:24]([CH2:27][O:28][C:29]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:25][OH:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>N1C=CC=CC=1>[CH2:6]([O:22][CH2:23][CH:24]([CH2:25][O:26][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:27][O:28][C:29]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 212991503-Hexadecyloxy-2-triphenylmethoxymethylpropan-1-ol

Product 1

HCID 212991491-Hexadecyloxy-2-methanesulfonyloxymethyl-3-triphenylmethoxypropaneYield 99.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonylchloride (0.752 g, 6.57 mmol) was added to a solution of 4 (3.00 g, 5.26 mmol) in dry pyridine (15 ml). After 3 hours the solution was poured into ice water and the product was extracted 3 times with hexane. The hexane extracts were washed with cold 1M H saturated NaHCO3 and water, and dried over Na2SO4 and concentrated. Chromatography on silica gel using hexane-CH2Cl2 (1:1 v/v) afforded 3.40 g (99%) the title compound (9) as a waxy solid, m.p. 39°. NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26H, --CH2 --), 1.52 (m, 2H, OCH2CH2R), 2.28 (m, 1H, CH), 2.84 (s, 3H, --CH3), 3.19, 3.21 (ABX, 2H, JAB = 10 Hz, /JAX +JBX /=8 Hz, CH2OTr, 3.35 (t, 2H, J=6.5 Hz, --OCH2R), 3.48 (d, 2H, J=6 Hz, CH2OR), 4.39 (d, 2H, J=6 Hz, CH2OMs).

Workup

  1. extractionthe product was extracted 3 times with hexane
  2. washThe hexane extracts were washed with cold 1M H saturated NaHCO3 and water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6017bc83f89a4ecb91b4a66125f86e7a
Source dataset
uspto-grants-1988_08
Patent number
US04761404

Reaction notes

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