Carbon Dioxide → HCID 58493981, compound

HRID 2360480Notes

Reaction equation

HRID 2360480 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][OH:12])[CH:4]=[CH:3]1.C([Li])CCC.[C:18](=[O:20])=[O:19].O>C(OCC)C.CCCCCC>[OH:12][CH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:2]([CH3:1])[C:3]([C:18]([OH:20])=[O:19])=[CH:4]2

Participants

7

Reactant 4

HCID 280Carbon Dioxide2×HCID 962WaterHCID 24229741(1-Methyl-1H-indol-7-yl)methanolHCID 178418339Butyllithium

Product 1

HCID 58493981HCID 58493981, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

Under argon a solution of 4 g (1-methyl-1H-indol-7-yl)-methanol in 80 ml diethyl ether is added dropwise to 76 ml of a 1.6 M solution of n-butyllithium in hexane at 0° C., while the temperature does not exceed 35° C. Then the mixture is stirred for another 12 hours at ambient temperature and the solution thus obtained is poured onto 30 g of crushed dry ice in 100 ml diethyl ether. The mixture is stirred until all the dry ice has dissolved and the reaction is then stopped by the addition of 40 ml of water. The phases are separated and the organic phase is extracted twice with 20 ml of water. The combined aqueous phases are suction filtered and the filtrate is adjusted to pH 2 with concentrated hydrochloric acid. The solid precipitated is suction filtered and dried in vacuo.

Workup

  1. customdoes not exceed 35° C
  2. customthe solution thus obtained
  3. dissolutionhas dissolved
  4. customThe phases are separated
  5. extractionthe organic phase is extracted twice with 20 ml of water
  6. filtrationfiltered
  7. customThe solid precipitated
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a5ee6624cb604bbf90ad9fa78ba67e81
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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