p-Toluenesulfonic acid → HCID 15661455, compound

HRID 1493854Notes

Reaction equation

HRID 1493854 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:19][OH:20])[C:8]2[CH:9]([OH:18])[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:19][O:20][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][O:21]2)[C:8]2[CH:9]([OH:18])[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 15661454HCID 15661454, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 15661455HCID 15661455, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxycarbonyl-1-hydroxymethyl-9-fluorenol (0.96 g) was treated with dihydropyran (0.43 ml) and p-toluenesulfonic acid (20 mg) in CH2Cl2 (20 ml) for 0.5 hour. The reaction mixture was washed once with NaHCO3 (10% soln) then dried and evaporated to give a mixture of products. Chromatography on silica gel using EtOAc/hexane 1:1 as eluant gave the product (403 mg).

Workup

  1. washThe reaction mixture was washed once with NaHCO3 (10% soln)
  2. customthen dried
  3. customevaporated
  4. customto give
  5. additiona mixture of products

Sources & evidence

ORD record
ord-c760c75c04924586adf943f245a2aca7
Source dataset
uspto-grants-1991_06
Patent number
US05025007

Reaction notes

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