Dichloromethane → (1-Chloro-3-((4-methoxybenzyl)oxy)propan-2-yl)(trityl)sulfane

HRID 2201224Notes

Reaction equation

HRID 2201224 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][O:8][CH2:9][CH:10]2[CH2:12][S:11]2)=[CH:5][CH:4]=1.[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl:35]CCl>>[Cl:35][CH2:12][CH:10]([S:11][C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:9][O:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 867234592-(((4-Methoxybenzyl)oxy)methyl)thiirane

Product 1

HCID 86723460(1-Chloro-3-((4-methoxybenzyl)oxy)propan-2-yl)(trityl)sulfane

Procedure

2-(((4-Methoxybenzyl)oxy)methyl)thiirane (496 mg, 2.359 mmol) was added to a solution of trityl chloride (598 mg, 2.144 mmol) in dichloromethane (10 mL). The mixture was stirred at room temperature for 16 hours, then evaporated under vacuum. Purification by chromatography on silica, eluting with 0-5% EtOAc/hexane, gave a crude material which was triturated with methanol to afford the title compound.

Workup

  1. customevaporated under vacuum
  2. customPurification by chromatography on silica
  3. washeluting with 0-5% EtOAc/hexane
  4. customgave a crude material which
  5. customwas triturated with methanol

Sources & evidence

ORD record
ord-3134e65ea8b04e1faec6a6ae2f61234e
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

Loading…