Methanol → 4-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1859314Notes

Reaction equation

HRID 1859314 reaction equation
CO.[Si:3]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[C:19][CH:20]1[C:29]2[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[S:23][CH2:22][C:21]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[CH3:32])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>[Pd].C(OCC)(=O)C>[Si:3]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[C:29]2[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[S:23][CH2:22][C:21]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[CH3:32])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 887MethanolHCID 220334284-[9-(t-Butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

Product 1

HCID 220332574-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methanol (60 ml) and 10% Pd/C (500 mg) were added to 4-[9-(t-butyl-dimethylsilyloxy)-1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (560 mg, 1.01 mmol) obtained in Example 28, and the mixture was stirred for 2 days under hydrogen gas (normal pressure). Ethyl acetate was added to the reaction solution which was then filtered, washed several times with ethyl acetate and concentrated under reduced pressure to remove the organic solvent. To the residue were added methanol (60 ml) and 10% Pd/C (300 mg), and the reaction mixture was stirred for 8 hours at 5 atomsphere under hydrogen gas. Ethyl acetate was added again to the reaction solution which was then filtered and concentrated under reduced pressure to obtain 450 mg (yield: 80%) of the title compound as an oil. The resulting compound was used in the next reaction without further purification.

Workup

  1. filtrationwas then filtered
  2. washwashed several times with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customto remove the organic solvent
  5. additionTo the residue were added methanol (60 ml) and 10% Pd/C (300 mg)
  6. stirringthe reaction mixture was stirred for 8 hours at 5 atomsphere under hydrogen gas
  7. additionEthyl acetate was added again to the reaction solution which
  8. filtrationwas then filtered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dbed4281149045a38163ad369e8317b9
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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