rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol → HCID 15171860, compound

HRID 256856Notes

Reaction equation

HRID 256856 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:18]([O:21][C:22]1[CH:27]=[C:26](I)[CH:25]=[CH:24][C:23]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:20])[CH3:19]>>[C:18]([O:21][C:22]1[CH:27]=[C:26]([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:25]=[CH:24][C:23]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6olHCID 15171858HCID 15171858, compound

Product 1

HCID 15171860HCID 15171860, compound

Procedure

This compound was obtained by coupling rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol with 5-iodo-2-(phenylmethoxy)phenyl acetate under the conditions described in Example 26. The crude product was chromatographed over the 50 fold amount of silica gel using methylene chloride. The combined fractions were evaporated and the residue was crystallized from methanol after treatment with charcoal and was recrystallized from ether/hexane for analysis to give colorless crystals with m.p. 117°-120°.

Workup

  1. customThis compound was obtained
  2. customThe crude product was chromatographed over the 50 fold amount of silica gel
  3. customThe combined fractions were evaporated
  4. customthe residue was crystallized from methanol after treatment with charcoal
  5. customwas recrystallized from ether/hexane for analysis
  6. customto give colorless crystals with m.p. 117°-120°

Sources & evidence

ORD record
ord-9308983f7e1442bdba9658903b5d5d2e
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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