Pyridine → Toluene-4-sulfonic acid Chroman-3-ylmethyl ester

HRID 984122Notes

Reaction equation

HRID 984122 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11][OH:12])[CH2:2]1.[C:13]1(C)[C:14]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=1.N1C=CC=C[CH:25]=1>>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11][O:12][S:19]([C:14]2[CH:13]=[CH:18][C:17]([CH3:25])=[CH:16][CH:15]=2)(=[O:20])=[O:21])[CH2:2]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 27954603,4-dihydro-2H-chromen-3-ylmethanol

Product 1

HCID 11267124Toluene-4-sulfonic acid Chroman-3-ylmethyl ester

Procedure

Compound 18A (3.6 g) was dissolved in pyridine (11 mL) at RT. Toluene sulfonyl chloride (4.5 g) was added, stirred for 6 h. The reaction mixture was quenched with 2N HCl (500 mL), ether extraction (2×200 mL). The combined ether was washed with water, brine, dried (MgSO4), concentrated, to afford an orange color solid, compound 18B (4.2 g). mp 83-84° C.; MS: 319 (M+1)+. Preparation of Chroman-3-yl-acetonitrile (Compound 18C)

Workup

  1. customThe reaction mixture was quenched with 2N HCl (500 mL), ether extraction (2×200 mL)
  2. washThe combined ether was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-87b4f8888764442ea93403e8a0251be4
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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