7-(2-Propenyloxy)-2-naphthalenol → Binol

HRID 859091Notes

Reaction equation

HRID 859091 reaction equation
C(O[C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([OH:15])=[CH:12]2)=[CH:7][CH:6]=1)C=C>C1(C2C3C(=CC=CC=3)C=CC=2)C(O)=CC=C2C=1C=CC=C2.C(Cl)(Cl)(Cl)Cl>[CH:6]1[CH:7]=[C:8]2[CH:9]=[CH:10][C:11]([OH:15])=[C:12]([C:12]3[C:13]4[C:8](=[CH:7][CH:6]=[CH:5][CH:14]=4)[CH:9]=[CH:10][C:11]=3[OH:15])[C:13]2=[CH:14][CH:5]=1

Participants

4

Reactant 1

HCID 111716387-(2-Propenyloxy)-2-naphthalenol

Product 1

HCID 11762BinolYield 99%

Reagents, catalysts & solvents 2

HCID 27552601-(1-Naphthyl)-2-naphtholCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A reaction flask described in example 9 was charged with a solution of catalyst 1 c (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-allyloxy-2-naphthol (40 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 3i, Yield 99%. [[α]D25=−186.5 (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, 3.0 Hz, 2H, 2×HC (6)), 6.49 (s, 2H, 2×HC (8)), 5.08 (s, 2H, 2×OH), 3.66–3.78 (m, 4H, 4×OCH2), 1.58–1.67 (m, 4H, 4×OCH2CH2), 1.20–1.40 (m, 4H, 4×CH2CH3), 0.87–0.89 (t, 6H, 6×CH3). e.e. 95%.

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-cf1578f48e0c4448bf299da7fc80d0b9
Source dataset
uspto-grants-2006_12
Patent number
US07151070B2

Reaction notes

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