methyl 7-chloronaphthalene-1-carboxylate → HCID 68697042, compound

HRID 1876279Notes

Reaction equation

HRID 1876279 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=2)[CH:18]=[CH:17][CH:16]=1)=O>C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[C:24]2[C:19]([CH:18]=[CH:17][CH:16]=[C:15]2[CH2:13][OH:12])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 230778methyl 7-chloronaphthalene-1-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 68697042HCID 68697042, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0.7M diisobutylaluminium hydride solution in CH2Cl2 is added dropwise at −78° to 22 g of 7-chloro-naphthalene-1-carboxylic acid methyl ester in CH2Cl2. After stirring at −78° for 1 hour, the mixture obtained is warmed up to 0°, quenched with aq. 10% sodium tartrate solution and stirred for further few minutes. The organic phase obtained is separated, washed with brine, dried and solvent is evaporated. The residue obtained is purified by flash chromatography on silica gel (eluent: cyclohexane/EtOAc 8/1 to 4/1) and the title compound is obtained.

Workup

  1. customthe mixture obtained
  2. temperatureis warmed up to 0°
  3. customquenched with aq. 10% sodium tartrate solution
  4. stirringstirred for further few minutes
  5. customThe organic phase obtained
  6. customis separated
  7. washwashed with brine
  8. customdried
  9. customsolvent is evaporated
  10. customThe residue obtained
  11. customis purified by flash chromatography on silica gel (eluent: cyclohexane/EtOAc 8/1 to 4/1)

Sources & evidence

ORD record
ord-12f7825e0b1f4576a975f938b8d70ccf
Source dataset
uspto-grants-2012_11
Patent number
US08309596B2

Reaction notes

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