Hydrochloric Acid → HCID 59514335, compound

HRID 254558Notes

Reaction equation

HRID 254558 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:16][CH3:17])[CH:9]=[CH:8][CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.O.Cl>C1COCC1>[CH2:16]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:6]([CH2:4][OH:3])=[CH:7][CH:8]=[CH:9]2)[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 59514331HCID 59514331, compound

Product 1

HCID 59514335HCID 59514335, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-ethyl-naphthalene-1-carboxylic acid ethyl ester (1.04 g) in THF (30 ml) was cooled to 0° C. and treated with diisobutyl aluminium hydride solution (11.4 ml; 1.2 M in toluene). The reaction mixture was stirred for 2 hrs at r.t., then again cooled to 0° C. and treated with H2O (50 ml) and 0.1N HCl (50 ml). The mixture was extracted with EtOAc. The organics were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient cyclohexane→cyclohexane/EtOAc 4:1) to give (8-ethyl-naphthalen-1-yl)-methanol (769 mg) as white solid. MS (ISP): 187.3 ((M+H)+.).

Workup

  1. temperatureagain cooled to 0° C.
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel; gradient cyclohexane→cyclohexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-efc8610ef4ec46f98c1a05dfdc3b0ea0
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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