rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol → rac-3,4-Dihydro-6-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethynyl]-4-(trifluoroacetyl)-2H-1,4-benzoxazine

HRID 256858Notes

Reaction equation

HRID 256858 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].[F:18][C:19]([F:34])([F:33])[C:20]([N:22]1[C:27]2[CH:28]=[C:29](I)[CH:30]=[CH:31][C:26]=2[O:25][CH2:24][CH2:23]1)=[O:21]>>[OH:15][C:10]1[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]2[O:4][C:3]([C:1]#[C:2][C:29]3[CH:30]=[CH:31][C:26]4[O:25][CH2:24][CH2:23][N:22]([C:20](=[O:21])[C:19]([F:33])([F:18])[F:34])[C:27]=4[CH:28]=3)([CH3:17])[CH2:8][CH2:7][C:6]=2[C:9]=1[CH3:16]

Participants

3

Reactant 2

HCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6olHCID 15171865HCID 15171865, compound

Product 1

HCID 15171867rac-3,4-Dihydro-6-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethynyl]-4-(trifluoroacetyl)-2H-1,4-benzoxazine

Procedure

This compound was prepared by coupling rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol (1,15 g or 5 mmol) with 4-(trifluoroacetyl)-3,4-dihydro-6-iodo-2H-1,4-benzoxazine (1.95 g or 5.5 mmol) under the conditions described in Example 15. The product was isolated by chromatography over the 40 fold amount of silica gel methylene chloride. It was crystallized from ether/hexane and recrystallized twice from methanol to give colorless crystals with m.p. 153°-155°.

Workup

  1. customThis compound was prepared
  2. customThe product was isolated by chromatography over the 40 fold amount of silica gel methylene chloride
  3. customIt was crystallized from ether/hexane
  4. customrecrystallized twice from methanol
  5. customto give colorless crystals with m.p. 153°-155°

Sources & evidence

ORD record
ord-8b38c198e7894597b1a71b6c4b3c140c
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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