HCID 85199645, compound → HCID 85259566, compound

HRID 399318Notes

Reaction equation

HRID 399318 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH:5]1([CH:11]2[CH:15]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[O:14][B:13]([CH:22](Cl)[CH:23]([CH3:31])[CH2:24][CH:25]([CH3:30])[C:26]([CH2:28][CH3:29])=[CH2:27])[O:12]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C1COCC1>[CH:16]1([CH:15]2[CH:11]([CH:5]3[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]3)[O:12][B:13]([CH:22]([CH2:1][CH3:2])[CH:23]([CH3:31])[CH2:24][CH:25]([CH3:30])[C:26]([CH2:28][CH3:29])=[CH2:27])[O:14]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 85199645HCID 85199645, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 85259566HCID 85259566, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Ethylmagnesium bromide (3.0 M in diethyl ether, 35.6 mmol) was added dropwise in 20 minutes to a stirred solution of [4R- [2(S*,S*,S*),4α,5β]]-4,5-dicyclohexyl-2-(6-chloro-2-ethyl-3,5-dimethylhexen-6-yl) -1,3,2-dioxaborolane (14.5 g, 35.6 mmol) in THF (200 mL) cooled with a -78° C. bath. The bath was allowed to warm to 20°-25° C. and the mixture was stirred for 24 h. The solution was concentrated under vacuum and ether (200 mL) was added to the residue. The ethereal solution was washed with saturated aqueous ammonium chloride (2∞200 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to liquid [4R-[2(S*,S*,S*),4α,5β]]-4,5-dicyclohexyl -2-(2,6-diethyl-3,5-dimethylhexen-6-yl)-1,3,2-dioxaborolane (14a) as a liquid (12.9 g, 90%); 300 MHz 1H-NMR (CDCl3) δ0.87-2.27 (m, 43), 3.81 (m, 2), 4.66 and 4.71 (AB, 2); 75 MHz 13C-NMR (CDCl3): 12.3, 14.1, 17.6, 19.5, 22.0, 25.8, 25.9, 26.1, 27.1, 27.6, 28.2, 28.5, 31.6, 37.4, 43.1, 83.1, 105.8, 156.8. HRMS: calcd for C26H48BO2 [(M+1)+] 403.3747; found, 403.3732.

Workup

  1. temperatureto warm to 20°-25° C.
  2. concentrationThe solution was concentrated under vacuum and ether (200 mL)
  3. additionwas added to the residue
  4. washThe ethereal solution was washed with saturated aqueous ammonium chloride (2∞200 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum to liquid [4R-[2(S*,S*,S*),4α,5β]]-4,5-dicyclohexyl -2-(2,6-diethyl-3,5-dimethylhexen-6-yl)-1,3,2-dioxaborolane (14a) as a liquid (12.9 g, 90%)

Sources & evidence

ORD record
ord-4349d8208d0146bab5c12315e85d2f1b
Source dataset
uspto-grants-1998_10
Patent number
US05817882

Reaction notes

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