Lithium borohydride → HCID 12272805, compound

HRID 268674Notes

Reaction equation

HRID 268674 reaction equation
C([O:3][C:4](=O)[C:5]([C:7]1[C:15]2[C:10](=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=O)C.[BH4-].[Li+]>O1CCCC1>[CH:16]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:5][CH2:4][OH:3])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 12272804Ethyl 7-(1-methylethyl)-α-oxo-1H-indole-3-acetate

Product 1

HCID 12272805HCID 12272805, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of (7-isopropyl-1H-indol-3-yl)-oxo-acetic acid ethyl ester (0.97 g. 3.7 mmol) in tetrahydrofuran was added 2.0 M solution of lithium borohydride in tetrahydrofuran. The mixture was heated at 90° C. for 5 hours. It was quenched with 5% HCl, followed by saturated sodium bicarbonate. It was extracted with ethyl acetate. The extracts were dried over magnesium sulfate and evaporated to dryness to provide a crude 2-(7-isopropyl-1H-indol-3-yl)-ethanol. ESI (+) MS m/e=204 (MH+), ESI (−) MS m/e=202 (MH−).

Workup

  1. customIt was quenched with 5% HCl
  2. extractionIt was extracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e8bda693b9704b21a2dde45d77a26463
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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