7-Ethoxy-2-naphthalenol → Binol

HRID 859088Notes

Reaction equation

HRID 859088 reaction equation
C(O[C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([OH:14])=[CH:11]2)=[CH:6][CH:5]=1)C>C1C2C(=CC=CC=2)C=CC=1O.C(Cl)(Cl)(Cl)Cl>[CH:5]1[CH:6]=[C:7]2[CH:8]=[CH:9][C:10]([OH:14])=[C:11]([C:11]3[C:12]4[C:7](=[CH:6][CH:5]=[CH:4][CH:13]=4)[CH:8]=[CH:9][C:10]=3[OH:14])[C:12]2=[CH:13][CH:4]=1

Participants

4

Reactant 1

HCID 122494857-Ethoxy-2-naphthalenol

Product 1

HCID 11762BinolYield 99%

Reagents, catalysts & solvents 2

HCID 86632-NaphtholCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A reaction flask described in example 9 was charged with a solution of catalyst 1c (12.2 mg, 0.02 mmol) in anhydrous CCl4 (1 mL). The solution was stirred for 10 min under an oxygen atmosphere and then treated with a solution of 7-ethoxy-2-naphthol (38 mg, 0.2 mmol) in anhydrous CCl4 (1 mL) under 0° C. The reaction mixture was stirred at 0° C. until the reaction was complete (monitored by TLC). The crude mixture was concentrated under reduced pressure, and purified by column chromatography (Ethyl acetate/Petroleum ether=⅓) to give (R)-BINOL 3e, Yield 99%. [α]D25=−154.0 (c=0.4 in EtOAc), 1HNMR (300 MHz, CDCl3) δ (ppm) 7.87 (d, J=9.0 Hz, 2H, 2×HC (5)), 7.78 (d, J=9.0 Hz, 2H, 2×HC (4)), 7.21 (d, J=9.0 Hz, 2H, 2×HC (3)), 7.03 (dd, J=9.0 Hz, 2.4 Hz, 2H, 2×HC (6)), 6.49 (d, J=2.1 Hz, 2H, 2×HC (8)), 5.06 (s, 2H, 2×OH), 3.78 (m, 4H, 4×OCH2), 1.28 (t, 6H, 6×CH3). e.e. 96%.

Workup

  1. customA reaction flask described in example 9
  2. stirringThe reaction mixture was stirred at 0° C. until the reaction
  3. concentrationThe crude mixture was concentrated under reduced pressure
  4. custompurified by column chromatography (Ethyl acetate/Petroleum ether=⅓)

Sources & evidence

ORD record
ord-5f8381df3e0a4befb39dcc029a6ea6ce
Source dataset
uspto-grants-2006_12
Patent number
US07151070B2

Reaction notes

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