Ethyl Acetate → rac-3,4-Dihydro-2-[(4-hydroxy-3-propylphenyl)ethynyl]-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol

HRID 654502Notes

Reaction equation

HRID 654502 reaction equation
[C:1]([C:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2].C([O:21][CH2:22][CH3:23])(=O)C>C(Cl)Cl>[OH:21][C:22]1[CH:23]=[CH:2][C:1]([C:2]#[C:1][C:3]2([CH3:17])[CH2:8][CH2:7][C:6]3[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=3[O:4]2)=[CH:3][C:8]=1[CH2:7][CH2:6][CH3:5]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol

Product 1

HCID 15171853rac-3,4-Dihydro-2-[(4-hydroxy-3-propylphenyl)ethynyl]-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was obtained by reacting rac-3,4-dihydro2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol with 4-iodo-2-propylphenyl under the conditions described in Example 1. The product was isolated by chromatography over the 40 fold amount of silica gel using 10% (V/V) of ethyl acetate in methylene chloride. It was crystallized from ether/hexane to give off-white crystals with m.p. 154°-156°.

Workup

  1. customThis compound was obtained
  2. customIt was crystallized from ether/hexane
  3. customto give off-white crystals with m.p. 154°-156°

Sources & evidence

ORD record
ord-f8e5b06e666b42ba8f9efe5f5e73832c
Source dataset
uspto-grants-1992_07
Patent number
US05132310

Reaction notes

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