HCID 43143668, compound → Binol

HRID 859092Notes

Reaction equation

HRID 859092 reaction equation
C(O[C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([OH:20])=[CH:17]2)=[CH:12][CH:11]=1)CCCCCCC>C1C2C(=CC=CC=2)C=CC=1O.C(Cl)(Cl)(Cl)Cl>[CH:11]1[CH:12]=[C:13]2[CH:14]=[CH:15][C:16]([OH:20])=[C:17]([C:17]3[C:18]4[C:13](=[CH:12][CH:11]=[CH:10][CH:19]=4)[CH:14]=[CH:15][C:16]=3[OH:20])[C:18]2=[CH:19][CH:10]=1

Participants

4

Reactant 1

HCID 43143668HCID 43143668, compound

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-octyloxy-2-naphthol (54 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 3j, Yield 99%. [α]D25=−153.8 (c=0.5 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)), 5.07 (s, 2H, 2×OH), 3.67–3.77 (m, 4H, 4×OCH2), 1.59–1.66 (m, 4H, 4×OCH2CH2), 1.25–1.29 (m, 20H, 20×CH2), 0.86–0.90 (t, 6H, 6×CH3). e.e. 94%.

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-333fcadbf5c34902803085f7c02a68b8
Source dataset
uspto-grants-2006_12
Patent number
US07151070B2

Reaction notes

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