Diethyl benzylphosphonate → HCID 58986363, compound

HRID 420807Notes

Reaction equation

HRID 420807 reaction equation
[CH2:1](P(=O)(OCC)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH2:24]([N:31]1[C:39]2[C:34](=[CH:35][C:36]([O:40][CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)=[CH:37][CH:38]=2)[C:33]([CH:47]=O)=[C:32]1[CH:49]([CH3:51])[CH3:50])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.CCOC(C)=O>[CH2:24]([N:31]1[C:39]2[C:34](=[CH:35][C:36]([O:40][CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)=[CH:37][CH:38]=2)[C:33](/[CH:47]=[CH:1]/[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:32]1[CH:49]([CH3:51])[CH3:50])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14122Diethyl benzylphosphonateHCID 2724682Lithium diisopropylamideHCID 58986346HCID 58986346, compound2×

Product 1

HCID 58986363HCID 58986363, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a −78° C. solution of diethyl benzylphoshonate (91 mg, 0.4 mmol) in THF (5 mL) was added a 2 M solution of LDA and THF (0.2 mL, 0.4 mmol), and the solution was warmed to RT over 20 min. A solution of 1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxaldehyde (Compound 13, 100 mg, 0.27 mmol) and THF (2 mL) was added, and the solution was stirred for 1 h at ambient temperature. The solution was diluted with EtOAc (50 mL), and washed with brine (10 mL), and dried (Na2SO4), and the solvent was removed under vacuum. Silica gel flash chromatography using 20% EtOAc in hexane gave (E)-1-benzyl-2-isopropyl-3-(2-phenylethen-1-yl)-5-(tetrahydropyran-2-yloxy)-1H-indole (Compound 26) as a colorless oil.

Workup

  1. washwashed with brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-72246d91b3364a83823c09543b48eca5
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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