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Lithium Hydroxide → HCID 66766833, compound

HRID 2195507
Notes
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Reaction equation

HRID 2195507 reaction equation
C([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:8][C:7]=1[O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=1[F:31])=[O:5])C.[Li+].[OH-].CCOC(C)=O.C(O)(=O)C>C1COCC1.CO.O>[F:31][C:23]1[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=[CH:27][C:22]=1[O:21][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:6]=1[C:4]([OH:5])=[O:3])[N:12]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[N:11]=[CH:10]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 22609514Ethyl acetate acetateHCID 66767080HCID 66767080, compound

Product 1

HCID 66766833HCID 66766833, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-6-carboxylate (22 g, 51.2 mmol) in THF (60 mL) and MeOH (60 mL) and H2O (10 mL) is added LiOH (3 g, 125 mmol). The resulting solution is stirred at RT for 1.5 hours and the organic solvents are removed. The aqueous residue is acidified with cold 6N HCl to pH 2, and extracted with EtOAc (150 mL). The organic phase is separated, dried, and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc:acetic acid (100:100:1) to afford the product (19.5 g, 95% yield). MS (m/z): 402.1 (M+H).

Workup

  1. customthe organic solvents are removed
  2. extractionextracted with EtOAc (150 mL)
  3. customThe organic phase is separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography
  7. washeluting with PE

Sources & evidence

ORD record
ord-6f2463e74cb9424282a0d982be44ce9b
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE043878E1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes