2-Naphthalenecarboxaldehyde → HCID 15323124, compound

HRID 489502Notes

Reaction equation

HRID 489502 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[N+:13]([CH3:16])([O-:15])=[O:14].C(N(C(C)C)CC)(C)C.C1COCC1>ClCCl.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:12])[CH2:16][N+:13]([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 62012-NaphthalenecarboxaldehydeHCID 6375NitromethaneHCID 8028TetrahydrofuranHCID 81531Diisopropylethylamine

Product 1

HCID 15323124HCID 15323124, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

A solution of N,N′-bis[2-(2,4,6-trimethylbenzoyl)-3-oxobutylidene]-(1S,2S)-bis(3,5-dimethylphenyl)ethylene-1,2-diaminato cobalt (II) complexes (7.53 mg, 0.01 mmol, 2 mol %; formula (c-4)) in dichloromethane (2.0 ml) was added into a reaction vessel at room temperature under a nitrogen atmosphere, and was cooled to −70° C. Thereafter, to the reaction vessel were added a solution of 2-naphthaldehyde (78.1 mg, 0.5 mmol) in dichloromethane (1.0 ml), a mixture of nitromethane (1.0 ml, 18.5 mmol) and dichloromethane (1.0 ml), and diisopropylethylamine (64.7 mg, 0.5 mmol) in this order. The reaction mixture was stirred for 76 hours, and THF containing water was then added into the reaction mixture to stop the reaction. After a usual aftertreatment was performed, the resultant crude product was separated and purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give 1-(2-naphthyl)-2-nitroethanol (89.7 mg, yield 83%). The optical purity of the product was analyzed by high performance liquid chromatography (optical activation column: Chiralpak AD-H manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.; EtOH 10% in hexane, flow rate 1.0 ml/min, 254 nm; retention time (−)-isomer 25.1 min, (+)-isomer 30.2 min). As a result, the optical purity was 81% ee. The specific rotation [α]D29 was −30.4° (c 0.90, CH2Cl2).

Workup

  1. additionwas then added into the reaction mixture
  2. customthe reaction
  3. customthe resultant crude product was separated
  4. custompurified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a33ec42c2c1b4254988c94f990d931ff
Source dataset
uspto-grants-2005_12
Patent number
US06977315B2

Reaction notes

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