Boron Trichloride → HCID 86658449, compound

HRID 468223Notes

Reaction equation

HRID 468223 reaction equation
C([O:8][CH2:9][C@H:10]([O:31][C:32](=[O:48])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[CH2:13]([O:12][CH2:11][C@H:10]([CH2:9][OH:8])[O:31][C:32](=[O:48])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 67436289HCID 67436289, compound

Product 1

HCID 86658449HCID 86658449, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-O-benzyl-1-O-oleyl-2-O-palmitoyl-sn-glycerol (110 mg, 0.16 mmol) in 2 mL CH2Cl2 at −78° C., boron trichloride (0.35 mL, 0.35 mmol) (1 M in CH2Cl2) was added over a period of 15 min. The reaction was stirred for 30 min under argon. The contents of the flask were then poured over ice water, the aqueous layer separated and extracted with CH2Cl2 (10 mL×3), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified using silica gel column chromatography (hexane:EtOAc=19:1˜7:1 (Rf=0.35) gradient) to get the alcohol (66 mg, 69%) as colorless oil. [α]D27 −3° (C=1.1, CHCl3); IR(CHCl3) cm−1 3442, 2911, 2853, 1736, 1652, 1460, 1374, 1239, 1167, 1116, 1094, 1053, 722, 700 cm−1; 1H NMR (600 MHz, CDCl3) δ 0.88 (t, J=7.2 Hz, 6H, CH3), 1.22-1.36 (m, 44 H, CH2), 1.52 (dt, J=7.2, 14.4 Hz, 4H, CH2), 1.94 (dd, J=6.0, 12.0 Hz, 4H, CH2), 2.05 (s, 1H, OH), 2.20 (t, J=7.8 Hz, 2H, CH2), 2.24 (t, J=7.8 Hz, 2H, CH2), 3.72 (s, 2H, CH2OH), 4.25 (dd, J=6.0, 12.0 Hz, 1H, CH2O Acyl), 4.31 (dd, J=4.8, 12.0 Hz, 1H, CH2OAcyl), 4.00-4.06 (dt, J=4.8, 10.2 Hz, 1H, CH), 5.35 (ddd, J=6.0, 10.8, 16.2 Hz, 2H, CH═CH); 13C NMR (150 MHz, CDCl3) δ 14.1, 22.66, 22.67, 24.78, 24.82, 24.84, 24.91, 27.14, 27.19, 29.06, 29.08, 29.15, 29.25, 29.30, 29.46, 29.50, 29.60, 29.63, 29.66, 29.67, 29.71, 29.74, 31.83, 31.88, 31.90, 34.1, 34.3, 61.5, 62.0, 72.1, 129.7, 130.0, 173.4, 173.8; EMSI calc'd for C37H70NaO5 [M+Na]+ 617.51. found: 617.60.

Workup

  1. customthe aqueous layer separated
  2. extractionextracted with CH2Cl2 (10 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-b25455e322fd4464b51e956d7d46265a
Source dataset
uspto-grants-2014_01
Patent number
US08624006B2

Reaction notes

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