Tetrahydrofuran → HCID 67973427, compound

HRID 623943Notes

Reaction equation

HRID 623943 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][O:13][C:14]1[CH:56]=[CH:55][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[N:31]=[CH:30][C:29]([C:32]4[N:33]([CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])[CH:34]=[C:35]([C:37](OCC5C=CC=CC=5)=[O:38])[N:36]=4)=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[N:31]=[CH:30][C:29]([C:32]4[N:33]([CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:53])([CH3:52])[CH3:54])[CH:34]=[C:35]([CH2:37][OH:38])[N:36]=4)=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)=[CH:55][CH:56]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67973593HCID 67973593, compound

Product 1

HCID 67973427HCID 67973427, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran (40 mL) suspension of lithium aluminum hydride (0.24 g) was added dropwise a tetrahydrofuran (30 mL) solution of benzyl 2-(6-{4-[(4-methoxybenzyl)oxy]phenyl}pyridin-3-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-4-carboxylate (2 g) under ice-cooling. After stirring for 30 minutes, sodium sulfate (720 mg) and water (0.48 mL) were added to the mixture. The mixture was stirred at room temperature for 1 hour, and filtered. The filtrate was concentrated under reduced pressure, the obtained residue was pulverized by adding ether, and collected by filtration to obtain [2-(6-{4-[(4-methoxybenzyl)oxy]phenyl}pyridin-3-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-4-yl]methanol.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionby adding ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-053ba939b7c147b09228e129fb7c2b88
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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