Citric Acid → HCID 67131240, compound

HRID 1678699Notes

Reaction equation

HRID 1678699 reaction equation
[Br-].[C:2]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)([O:4][CH3:5])=[O:3].CC(C)([O-])C.[K+].[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[C:53]([CH:54]([CH:57]3[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]3)[CH:55]=O)=[C:52]3[C:47]([CH2:48][CH2:49][CH2:50][CH2:51]3)=[N:46]2)=[CH:41][CH:40]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O.CCOC(C)=O>[CH3:5][O:4][C:2](=[O:3])[C:6]1[CH:7]=[CH:8][C:9](/[CH:10]=[CH:55]/[CH:54]([C:53]2[N:45]([C:42]3[CH:43]=[CH:44][C:39]([Cl:38])=[CH:40][CH:41]=3)[N:46]=[C:47]3[C:52]=2[CH2:51][CH2:50][CH2:49][CH2:48]3)[CH:57]2[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]2)=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 23665647Potassium tert-butoxideHCID 87281415HCID 87281415, compound

Product 1

HCID 67131240HCID 67131240, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 379 mg (0.772 mmol) 4-carbomethoxybenzyl triphenylphosphonium bromide ([1253-46-9]) in 6 ml THF was added 87 mg (0.772 mmol) potassium tert-butoxide at 0° C. The reaction mixture was stirred for 15 minutes at 0° C. [2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetaldehyde (0.772 mmol; 1 eq.) was added at 0° C. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was poured on 30 ml citric acid 10% in H2O and 30 ml EtOAc. The aqueous layer was extracted a second time with 30 ml EtOAc. The combined organic layers were washed with 30 ml brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (20 g silica gel; gradient: n-heptane:EtOAc) to give the title compound.

Workup

  1. additionwas added at 0° C
  2. extractionThe aqueous layer was extracted a second time with 30 ml EtOAc
  3. washThe combined organic layers were washed with 30 ml brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography (20 g silica gel; gradient: n-heptane:EtOAc)

Sources & evidence

ORD record
ord-45c620dfc9c84a628c7065986b3c05b0
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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