Methyl 6-formyl-1-naphthoate → HCID 66660719, compound

HRID 472787Notes

Reaction equation

HRID 472787 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=[CH:6]2)=[O:2].[CH2:17]([Mg]Br)[CH2:18][CH2:19][CH2:20][CH3:21]>CCOCC>[OH:2][CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=[CH:6]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 58056979Methyl 6-formyl-1-naphthoateHCID 178445865HCID 178445865, compound

Product 1

HCID 66660719HCID 66660719, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl 6-formyl-1-naphthoate (36 mg, 0.17 mmol) in THE (1.7 mL) was cooled to 0° C. and treated with n-pentylmagnesium bromide (0.1 mL of a 2.0 M solution in Et2O, 0.2 mmol). The cooling bath was removed and after stirring at room temperature for 1 h the reaction was quenched with 1 N aqueous HCl, diluted with water (10 mL) and extracted with EtOAc (3×10 The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified on 12 g silica gel (100% hexanes→40% EtOAc/hexanes, gradient) to afford 34 mg (71%) of methyl 6-(1-hydroxyhexyl)-1-naphthoate.

Workup

  1. customThe cooling bath was removed
  2. customwas quenched with 1 N aqueous HCl
  3. additiondiluted with water (10 mL)
  4. extractionextracted with EtOAc (3×10 The combined organic phase
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified on 12 g silica gel (100% hexanes→40% EtOAc/hexanes, gradient)

Sources & evidence

ORD record
ord-419b4ccd0db946f99227bb7681fe07a1
Source dataset
uspto-grants-2014_01
Patent number
US08633220B2

Reaction notes

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