Boron Trichloride → HCID 10738692, compound

HRID 363502Notes

Reaction equation

HRID 363502 reaction equation
[C:1]([O:4][CH2:5][C:6]1([CH2:26][O:27]CC2C=CC=CC=2)[CH2:10][O:9][C:8](=[O:11])/[C:7]/1=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:3])[CH3:2].B(Cl)(Cl)Cl>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1([CH2:26][OH:27])[CH2:10][O:9][C:8](=[O:11])/[C:7]/1=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 10719248HCID 10719248, compound

Product 1

HCID 10738692HCID 10738692, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14b (0.324 g, 0.685 mmol) in CH2Cl2 (20 mL) was cooled to -78° C., treated with boron trichloride (1.0M in dichloromethane, 2.74 mL, 2.74 mmol), and stirred for 1 h at that temperature. The reaction mixture was quenched with saturated NaHCO3 solution (3.0 mL), and immediately partitioned between chloroform and a pH 7 buffer solution. The organic layer was washed with water, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography over silica gel with EtOAc/hexane (1:1) as eluant to give 14c (0.252 g, 96%) as a white solid: mp 48° C.; IR (KBr) 3489 (OH), 1735 (C=O) and 1667 cm-1 (C=C); 1H NMR (CDCl3) δ 0.86 (distorted t, 3 H, CH3), 1.10-1.50 (m, 22 H, >C=CHCH2 (CH2)11CH3), 2.08 (s, 3 H, CH3CO), 2.60-2.90 (m, 2 H, >C=CHCH2), 3.59 (AB m, 2 H, CH2OH), 4.18 (2 AB multiplets, 4 H, H-5, CH2OAc), 6.28 (t, 1 H, J=7.6 Hz, 1 H, >C=CH); 13C NMR (CDCl3) δ 14.11, 20.72, 22.68, 27.61, 29.06, 29.24, 29.35, 29.41, 29.55, 29.64, 31.91, 47.58, 64.42, 65.34, 69.86, 126.06, 147.72, 169.69, 171.19; FAB MS m/z 383 (MH+, 100). Anal. Calcd for C22H38O5 : C, 69.07; H, 10.01. Found: C, 69.06; H: 10.03.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution (3.0 mL)
  2. customimmediately partitioned between chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography over silica gel with EtOAc/hexane (1:1) as eluant

Sources & evidence

ORD record
ord-eb8af8034e234c42affad88ede78f94d
Source dataset
uspto-grants-1999_02
Patent number
US05874464

Reaction notes

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