Methanol → HCID 69270322, compound

HRID 751497Notes

Reaction equation

HRID 751497 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:20]([CH3:22])[CH3:21])[CH:15]=[CH:14]2)([CH3:4])([CH3:3])[CH3:2].N1C(C)=CC=CC=1C.C(Cl)(=O)[C:34](Cl)=[O:35].[CH3:39][OH:40].[CH3:41][O-:42].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:39][O:40][C:34](=[O:35])[C:41]([C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:24])[CH3:23])[CH:12]=2)[N:16]([CH:20]([CH3:21])[CH3:22])[CH:15]=1)=[O:42]

Participants

8

Reactant 5

HCID 887MethanolHCID 79372,6-LutidineHCID 65578Oxalyl chlorideHCID 10942334Sodium MethoxideHCID 69268875HCID 69268875, compound

Product 1

HCID 69270322HCID 69270322, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve 5-[3-(tert-butyldimethyl-silyloxy)propoxy]-1-isopropyl-1H-indole (0.43 g, 1.124 mmol) in tetrahydrofuran (40 mL). Add 2,6-lutidine (0.43 mL, 3 eq) and cool to 0° C. Add oxalyl chloride dropwise and stir for 1.5 hours then cool to −78° C., add methanol (0.1 mL, 2 eq) and treated with sodium methoxide (25% w/w in methanol, 22.5 mL). Stir for 1 hour then dilute with ethyl acetate and extract with saturated sodium bicarbanate then brine. Dry over magnesium sulfate, filter and concentrate. Purification by column chromatography (4:1 hexanes:ethyl acetate) affords the title compound as a light yellow oil. MS (ES, m/z): 434.3 (M+1).

Workup

  1. extractionextract with saturated sodium
  2. dry with materialDry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurification by column chromatography (4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-81f1b4d81e964fe491621b83f018a46d
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

Loading…