Tetrahydrofuran → 3,4-Dihydro-2,5,7,8-tetramethyl-2-(2-phenylethyl)-2H-1-benzopyran-6-ol

HRID 654510Notes

Reaction equation

HRID 654510 reaction equation
[CH3:1][C:2]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7][CH2:6][C:5]2[C:8]([CH3:15])=[C:9]([OH:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1.O1CCCC1>[Pd].C(O)C>[CH3:1][C:2]1([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:7][CH2:6][C:5]2[C:8]([CH3:15])=[C:9]([OH:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 151718093,4-dihydro-2,5,7,8-tetramethyl-2-(2-phenylethynyl)-2H-1-benzopyran-6-ol

Product 1

HCID 151718903,4-Dihydro-2,5,7,8-tetramethyl-2-(2-phenylethyl)-2H-1-benzopyran-6-olYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.3 g (4.2 mmol) of 3,4-dihydro-2,5,7,8-tetramethyl-2-(2-phenylethynyl)-2H-1-benzopyran-6-ol (Example 1), 0.3 g of 5% palladium on carbon, 50 ml of tetrahydrofuran and 50 ml ethanol was hydrogenated at atmospheric pressure for 4 hours. The catalyst was filtered off and the filtrate was evaporated. Crystallization of the residue from hexane yielded 0.9 g (69 %) of colorless crystals with m.p. 96°-98°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customCrystallization of the residue from hexane

Sources & evidence

ORD record
ord-486c03fb120c4fc6bc6df6fde43cfdc6
Source dataset
uspto-grants-1992_07
Patent number
US05132310

Reaction notes

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