HCID 13938999, compound → Binol

HRID 859093Notes

Reaction equation

HRID 859093 reaction equation
C(O[C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([OH:24])=[CH:21]2)=[CH:16][CH:15]=1)CCCCCCCCCCC>C1C2C(=CC=CC=2)C=CC=1O.C(Cl)(Cl)(Cl)Cl>[CH:15]1[CH:16]=[C:17]2[CH:18]=[CH:19][C:20]([OH:24])=[C:21]([C:21]3[C:22]4[C:17](=[CH:16][CH:15]=[CH:14][CH:23]=4)[CH:18]=[CH:19][C:20]=3[OH:24])[C:22]2=[CH:23][CH:14]=1

Participants

4

Reactant 1

HCID 13938999HCID 13938999, compound

Product 1

HCID 11762BinolYield 94%

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-dodecyloxy-2-naphthol (66 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 3k, Yield 94%. [α]D25=−86.3 (c=0.2 in EtOAc), 1HNMR (300 MHz, CDCl3) δ (ppm) 7.86 (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, 2.1 Hz, 2H, 2×HC (6)), 6.49 (d, J=2.1 Hz, 2H, 2×HC (8)), 5.08 (s, 2H, 2×OH), 3.65–3.79 (m, 4H, 4×OCH2), 1.59–1.67 (m, 4H, 4×OCH2CH2), 1.25–1.27 (m, 36H, 36 ×CH2), 0.88–0.92 (t, 6H, 6×CH3). e.e. 97%.

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-c094a5dcffb44296b6601f0c62672f17
Source dataset
uspto-grants-2006_12
Patent number
US07151070B2

Reaction notes

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