Sulfuric acid magnesium salt (1:1) → HCID 11819612, compound

HRID 2081216Notes

Reaction equation

HRID 2081216 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12](OCC)=[O:13])=[CH:7]2.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([CH2:12][OH:13])=[CH:7]2

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium ChlorideHCID 19799267HCID 19799267, compoundHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 11819612HCID 11819612, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-fluoro-1-methyl-1H-indole-2-carboxylate (4.5 g) was dissolved in dry THF (50 ml), and cooled to -78° under nitrogen. Diisobutylaluminium hydride (DIBAL) (1M solution in hexane; 22.3 ml) was added and the mixture was stirred at -78° for 3 h, then allowed to warm to room temperature over 1 h. A further portion of DIBAL :(3 ml) was added to the recooled mixture at -78°, and stirring was continued for a further 16 h. Saturated ammonium chloride solution (10 ml) was added and the mixture was stirred for 30 min. Magnesium sulphate (dried, 10 g) was added, and the resultant mixture was filtered and evaporated in vacuo to leave an oil which was purified by FCC eluting with ether:hexane (1:1) to give the title compound (1.55 g) as a solid, m.p. 89°-91°.

Workup

  1. temperaturecooled to -78° under nitrogen
  2. stirringstirring
  3. waitwas continued for a further 16 h
  4. stirringthe mixture was stirred for 30 min
  5. filtrationthe resultant mixture was filtered
  6. customevaporated in vacuo
  7. customto leave an oil which
  8. customwas purified by FCC
  9. washeluting with ether:hexane (1:1)

Sources & evidence

ORD record
ord-3e735d1ece1e4f2abf3c746f4fb4ea9b
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

Loading…