4-Toluenesulfonyl chloride → HCID 58880520, compound

HRID 2251729Notes

Reaction equation

HRID 2251729 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:16][CH2:15][C:14]3[CH:17]=[C:18]([CH2:21]O)[CH:19]=[CH:20][C:13]=3[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.C1(C)C=CC(S([Cl:39])(=O)=O)=CC=1>ClCCl>[Cl:39][CH2:21][C:18]1[CH:19]=[CH:20][C:13]2[CH2:12][O:11][CH:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[O:16][CH2:15][C:14]=2[CH:17]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11536760HCID 11536760, compound

Product 1

HCID 58880520HCID 58880520, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g (5 mmol) of [7-(4-nitrophenyl)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl]methanol in 15 ml of dichloromethane are introduced into a flask. 0.76 g (7.5 mmol) of triethylamine is added and 1 g (5.4 mmol) of p-toluenesulfonyl chloride is added in small solid portions at room temperature. After 20 hours of reaction, the solvent is evaporated off and the crude product is purified by silica gel chromatography (heptane/ethyl acetate: 4/1) to give 0.6 g of 2-chloromethyl-7-(4-nitrophenyl)-(5H,9H)-6,8-dioxabenzocycloheptene.

Workup

  1. customAfter 20 hours of reaction
  2. customthe solvent is evaporated off
  3. customthe crude product is purified by silica gel chromatography (heptane/ethyl acetate: 4/1)

Sources & evidence

ORD record
ord-b9a2f78cd8164119b73135233d68e483
Source dataset
uspto-grants-2008_01
Patent number
US07319155B2

Reaction notes

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