1-Iodonaphthalene → rac-3,4-dihydro-2,5,7,8-tetramethyl-2-[(1-naphthyl)ethynyl]-2H-1-benzopyran-6-ol

HRID 256854

Reaction equation

HRID 256854 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].I[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:17][C:3]1([C:1]#[C:2][C:27]2[C:28]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:24]=[CH:25][CH:26]=2)[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

Participants

4

Reactant 2

HCID 70041-IodonaphthaleneHCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol

Product 1

HCID 15171855rac-3,4-dihydro-2,5,7,8-tetramethyl-2-[(1-naphthyl)ethynyl]-2H-1-benzopyran-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

rac-3,4-dihydro-2,5,7,8-tetramethyl-2-[(1-naphthyl)ethynyl]-2H-1-benzopyran-6-ol was prepared by coupling rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol with 1-iodonaphthalene under the conditions described in Example 1. It was isolated by chromatography over 40 fold amount of silica gel using methylene chloride. The combined clean fractions were crystallized from hexane and recrystallized from petroleum ether to give colorless crystals with m.p. 127°-128°.

Workup

  1. customIt was isolated by chromatography over 40 fold amount of silica gel
  2. customThe combined clean fractions were crystallized from hexane
  3. customrecrystallized from petroleum ether
  4. customto give colorless crystals with m.p. 127°-128°

Sources & evidence

ORD record
ord-c086264cb3754d7dbd62c47068519986
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Linked notes

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