4-Toluenesulfonyl chloride → (1-(Hydroxymethyl)cyclopent-3-en-1-yl)methyl 4-methylbenzenesulfonate

HRID 2203677Notes

Reaction equation

HRID 2203677 reaction equation
[C:1]1([CH2:8][OH:9])([CH2:6][OH:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.C(N(CC)CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:24][C:23]1[CH:25]=[CH:26][C:20]([S:17]([O:7][CH2:6][C:1]2([CH2:8][OH:9])[CH2:5][CH:4]=[CH:3][CH2:2]2)(=[O:19])=[O:18])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 14656537[1-(Hydroxymethyl)cyclopent-3-en-1-yl]methanol

Product 1

HCID 118161597(1-(Hydroxymethyl)cyclopent-3-en-1-yl)methyl 4-methylbenzenesulfonateYield 39%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
26 °C

Procedure

To an ice-cooled solution of cyclopent-3-ene-1,1-diyldimethanol (44.0 g, 343 mmol), triethylamine (34.7 g, 343 mmol) and 4-dimethylaminopyridine (4.19 g, 34.3 mmol) in dichloromethane (2 L) was added tosyl chloride (58.9 g, 309 mmol) portionwise. The reaction mixture was warmed to 26° C. After 16 h, the mixture was concentrated, and the resulting residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether)) to afford product as a brown solid (34 g, 35% yield).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe resulting residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether))

Sources & evidence

ORD record
ord-96893ea0bfb44876ab0b473432036c4c
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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