Tetrahydrofuran → (S)-2-{2[2-(1-methoxycarbonylethoxy)phenyl]vinyl}-1-methylindole

HRID 2148

Reaction equation

HRID 2148 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[N:11]([CH3:19])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC[O:41]C(/N=N/C(OCC)=O)=O.[CH2:51]1[CH2:55][O:54][CH2:53][CH2:52]1>[Cl-].[Na+].O>[CH3:55][O:54][C:53]([C@@H:52]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[N:11]([CH3:19])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:51])=[O:41]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 699556352-[2-(2-Hydroxyphenyl)vinyl]-1-methylindole

Product 1

HCID 69953350(S)-2-{2[2-(1-methoxycarbonylethoxy)phenyl]vinyl}-1-methylindoleYield 90%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1.50 g (6.02 mmol) of 2-[2-(2-hydroxyphenyl)vinyl]-1-methylindole, 1.89 g (7.21 mmol) of triphenylphosphine and 0.69 ml (7.22 mmol) of R-(+)-methyl lactate in 15 ml of THF was added 1.14 ml (7.24 mmol) of diethylazodicarboxylate under an ice-cooled condition, followed by stirring at room temperature for 2 hours. Brine was added to the reaction mixture, followed by extraction with methylene chloride. The extract was dried over Na2SO4, and evaporated. CHCl3 -n-hexane was added to the residue and, after filtration, the organic layer was purified by silica gel column chromatography (CHCl3 /n-hexane/AcOEt=10/10/1) to give 1.82 g (90%) of (S)-2-{2[2-(1-methoxycarbonylethoxy)phenyl]vinyl}-1-methylindole.

Workup

  1. temperaturecooled condition
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe extract was dried over Na2SO4
  4. customevaporated
  5. additionCHCl3 -n-hexane was added to the residue
  6. filtrationafter filtration
  7. customthe organic layer was purified by silica gel column chromatography (CHCl3 /n-hexane/AcOEt=10/10/1)

Sources & evidence

ORD record
ord-45b51dfa48a4401f8cc762580c573748
Source dataset
uspto-grants-1998_03
Patent number
US05728709

Linked notes

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