Boron Trichloride → HCID 86693881, compound

HRID 1504989Notes

Reaction equation

HRID 1504989 reaction equation
C([O:8][C@H:9]1[C:19]2([CH2:21][CH2:20]2)[C@H:18]2[C@@H:11]([O:12][Si:13]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[O:14][Si:15]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:16][CH2:17]2)[C@@H:10]1[F:34])C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[F:34][C@H:10]1[C@@H:11]2[O:12][Si:13]([CH:28]([CH3:30])[CH3:29])([CH:31]([CH3:33])[CH3:32])[O:14][Si:15]([CH:25]([CH3:26])[CH3:27])([CH:22]([CH3:23])[CH3:24])[O:16][CH2:17][C@H:18]2[C:19]2([CH2:21][CH2:20]2)[C@@H:9]1[OH:8]

Participants

4

Reactant 2

HCID 25135Boron Trichloride2×HCID 86693882HCID 86693882, compound

Product 1

HCID 86693881HCID 86693881, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 26 (1.38 g, 2.6 mmol) in anhydrous CH2Cl2 was treated with boron trichloride (7.1 ml, 1M solution in CH2Cl2, 8.1 mmol) at −78° C. during 15 minute. After stirred at the same temperature for another 15 min, additional portion of boron trichloride (5.1 mL of 1M solution in CH2Cl2) was added. The reaction was quenched with MeOH at −78° C. after 15 min and concentrated under reduced pressure. The residue was purified by column chromatography on the silica gel (EtOAc:Hexane=1;10 to 1:3) to give 27 (0.84 g, 78%). [α]24D−53.55° (c 0.5, MeOH); 1H NMR (500 MHz, CDCl3) δ 4.65 (dt, J=8.0 & 15.0 Hz, 1H), 4.49-4.45 (m, 1H), 4.26-4.21 (m, 1H), 3.99 (dd, J=4.5 & 12.0 Hz, 1H), 3.89 (dd, J=6.0 & 11.5 Hz, 1H), 2.66 (s, 1H), 0.93-1.08 (m, 28H), 0.72 (m, 1H), 0.68-0.43 (m, 2H), 0.28 (m, 1H); 19F NMR (500 MHz, CDCl3) δ −195.8 (m); 13C NMR (125 MHz, CDCl3) δ 7.8, 12.5, 12.7, 13.3, 13.4, 16.9, 16.98, 17.07, 17.08, 17.4, 17.5, 27.5 29.8, 49.1, 63.7, 73.7, 74.7, 102.3 (d, J=192.7 Hz); HR-MS Calcd. For (C20H39FO4Si2+H)+ 418.2592. found 418.2592.

Workup

  1. customThe reaction was quenched with MeOH at −78° C. after 15 min
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on the silica gel (EtOAc:Hexane=1;10 to 1:3)

Sources & evidence

ORD record
ord-363cd1ecbbb84bcbbe2d4467e0308ed9
Source dataset
uspto-grants-2015_12
Patent number
US09216960B2

Reaction notes

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