HCID 15187582, compound → HCID 10445237, compound

HRID 964499Notes

Reaction equation

HRID 964499 reaction equation
[CH3:1][C:2]1([CH3:19])[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[C:5]([CH3:18])([CH3:17])[CH2:4][CH2:3]1)[O:13][CH:12]=[CH:11][C:10]3=[O:16]>[Pd].CCOC(C)=O.CO>[CH3:1][C:2]1([CH3:19])[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[C:5]([CH3:18])([CH3:17])[CH2:4][CH2:3]1)[O:13][CH2:12][CH2:11][C:10]3=[O:16]

Participants

4

Reactant 1

HCID 15187582HCID 15187582, compound

Product 1

HCID 10445237HCID 10445237, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 6,6,9,9-tetramethyl-6,7,8,9-tetrahydrobenzo[g]chromen-4-one (4.4 g, 17.2 mmol) in 1:1 EtOAc/methanol (250 ml) containing 10% palladium on carbon (1:1 g, 7% by weight) was stirred at room temperature under an atmosphere of hydrogen (balloon) for 14 h. TLC analysis indicated complete reaction. The mixture was filtered and concentrated to give a yellow oil. The oil was passed through a small column of silica (10% EtOAc in hexane) and concentration to give 6,6,9,9-tetramethyl-2,3,6,7,8,9-hexahydrobenzo[g]chromen-4-one (4.2 g, 16.3 mmol, 95%) as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H), 6.86 (s, 1H), 4.46 (t, 2H), 2.75 (t, 2H), 1.65 (s, 4H), 1.25 (s, 12H).

Workup

  1. customreaction
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customto give a yellow oil
  5. concentrationThe oil was passed through a small column of silica (10% EtOAc in hexane) and concentration

Sources & evidence

ORD record
ord-8326c2f81756426891cdf7cde48808a7
Source dataset
uspto-grants-1998_06
Patent number
US05770378

Reaction notes

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