Sulfuryl chloride → 4-(Tetrahydropyran-4-yloxymethyl)-benzenesulfonyl chloride

HRID 2304261Notes

Reaction equation

HRID 2304261 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Li])CCC.[S:21](Cl)([Cl:24])(=[O:23])=[O:22].O1CCC(OC2C=CC(S(Cl)(=O)=O)=CC=2)CC1>>[O:11]1[CH2:12][CH2:13][CH:8]([O:7][CH2:6][C:5]2[CH:14]=[CH:15][C:2]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 24648Sulfuryl chlorideHCID 226656814-[(4-Bromophenyl)methoxy]tetrahydro-2H-pyranHCID 226657534-(Oxan-4-yloxy)benzene-1-sulfonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 226656724-(Tetrahydropyran-4-yloxymethyl)-benzenesulfonyl chloride

Procedure

This compound was prepared from 0.68 g of 4-(4-bromo-benzyloxy)-tetrahydropyran, 2 mL of n-butyllithium (1.6 N in hexane) and 0.81 mL of sulfuryl chloride using the procedure described for 58b. Yield: 0.70 g (oil), 1H-NMR (D6-DMSO): δ=1.41 (m, 2H), 1.86 (m, 2H), 3.32 (m, 2H), 3.54 (m, 1H), 3.79 (m, 2H), 4.53 (s, 2H), 7.30 (d, 2H), 7.61 (d, 2H).

Sources & evidence

ORD record
ord-7da2873493b247f98a937aabb45aa9bf
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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