HCID 89422926, compound → HCID 71284318, compound

HRID 1481763Notes

Reaction equation

HRID 1481763 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([CH:18]=[O:19])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([Mg]Cl)[CH2:22][CH3:23]>C1COCC1>[CH2:1]([O:8][C:9]1[C:17]([CH:18]([OH:19])[CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 89422926HCID 89422926, compoundHCID 178455855HCID 178455855, compound

Product 1

HCID 71284318HCID 71284318, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(benzyloxy)-1-methyl-1H-indole-5-carbaldehyde (4.57 g, 17.22 mmol) in THF (60 mL) at −78° C. was slowly added a solution of n-PrMgCl (2M Et2O, 13.00 mL, 26 mmol). The mixture was stirred at this temperature for 15 min and then allowed to warm to 0° C. After 1 h the reaction was quenched with NH4Cl (aqueous saturated, 50 mL) and the product was extracted with EtOAc (3×100 mL). The combined organics were washed with NaCl (aqueous saturated, 100 mL) and dried over Na2SO4. The solvents were concentrated to yield 1-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)butan-1-ol as an oil which was used directly in the next step without purification.

Workup

  1. customAfter 1 h the reaction was quenched with NH4Cl (aqueous saturated, 50 mL)
  2. extractionthe product was extracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with NaCl (aqueous saturated, 100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationThe solvents were concentrated

Sources & evidence

ORD record
ord-4c5f01db21674725ada6ba3a2bd1fc85
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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