HCID 22033151, compound → HCID 22033182, compound

HRID 1792339Notes

Reaction equation

HRID 1792339 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:46]=[CH:45][C:15]([O:16][CH2:17][C:18]#[C:19][CH:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH2:31][O:32][CH3:33])=[CH:27][CH:28]=3)[S:23][CH2:22][C:21]2([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:37][CH:36]=2)[CH3:34])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C>C(O)C.O1CCCC1.[OH-].[OH-].[Pd+2]>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:46]=[CH:45][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH2:31][O:32][CH3:33])=[CH:27][CH:28]=3)[S:23][CH2:22][C:21]2([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:37][CH:36]=2)[CH3:34])=[CH:14][CH:13]=1

Participants

5

Reactant 1

HCID 22033151HCID 22033151, compound

Product 1

HCID 22033182HCID 22033182, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-{3-[4-(2-t-Butyldimethylsilyloxyethoxy)phenoxy]-1-propynyl}-7-methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methylthiochroman (6) prepared in Step 4 (408 mg) was dissolved in a solvent mixture of ethanol (6 ml) and tetrahydrofuran (2 ml), 20% palladium hydroxide/carbon (130 mg) washed with ethanol was added, and the resulting mixture was stirred under hydrogen for 17 hours. The reaction solution was filtered through cellite, concentrated, and subjected to silica gel column chromatography to give 4-(3-[4-(2-hydroxyethoxy)phenoxy]propyl}-7-methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methylthiochroman (7) (241 mg, yield 71%) as a yellow oily substance.

Workup

  1. washwashed with ethanol
  2. additionwas added
  3. filtrationThe reaction solution was filtered through cellite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-53598c346723420eaeaa22f16cbfcda1
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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