1-[(Phenyl)methyl]-2-methyl-5-[(2-phenyl-4-thiazolyl)methoxy]-1H-indole-3-acetic acid → 5-[(2-Phenyl-4-thiazolyl)methoxy]-1-(phenylmethyl)-2-methyl-1H-indole-3-ethanol

HRID 37717Notes

Reaction equation

HRID 37717 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][C:25]4[N:26]=[C:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[S:28][CH:29]=4)=[CH:20][CH:21]=3)[C:16]([CH2:36][C:37](O)=[O:38])=[C:15]2[CH3:40])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[C:30]1([C:27]2[S:28][CH:29]=[C:25]([CH2:24][O:23][C:19]3[CH:18]=[C:17]4[C:22](=[CH:21][CH:20]=3)[N:14]([CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:15]([CH3:40])=[C:16]4[CH2:36][CH2:37][OH:38])[N:26]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 152880281-[(Phenyl)methyl]-2-methyl-5-[(2-phenyl-4-thiazolyl)methoxy]-1H-indole-3-acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 152880415-[(2-Phenyl-4-thiazolyl)methoxy]-1-(phenylmethyl)-2-methyl-1H-indole-3-ethanolYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry containing lithium aluminum hydride (0.10 g, 2.6mmol) in tetrahydrofuran (40 mL), is added slowly at 23° C. a solution of the ester of Example 40 (1.0 g, 2.0 mmol) in tetrahydrofuran (10 mL). After stirring for 1 hour, the excess lithium aluminum hydride is quenched with ethyl acetate (5.0 mL), poured into saturated sodium chloride (200 mL) and extracted with ether (200 mL, 2×). The ether layer is washed with brine, dried over MgSO4, and concentrated to give crude product (0.8 g). Crystallization of the solid from ethyl acetate affords 0.5 g of title compound as a white solid in 55% yield, m.p. 114°-116° C.

Workup

  1. customthe excess lithium aluminum hydride is quenched with ethyl acetate (5.0 mL)
  2. additionpoured into saturated sodium chloride (200 mL)
  3. extractionextracted with ether (200 mL, 2×)
  4. washThe ether layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give crude product (0.8 g)
  8. customCrystallization of the solid from ethyl acetate

Sources & evidence

ORD record
ord-2569115855054fa8a828b646bcbb4e9e
Source dataset
uspto-grants-1995_05
Patent number
US05420289

Reaction notes

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