1,3-Dichlorotetraisopropyldisiloxane → HCID 67433790, compound

HRID 1842841Notes

Reaction equation

HRID 1842841 reaction equation
Cl[Si:2]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[O:3][Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6].[CH2:18]([O:25][C@H:26]1[C:30](=[CH2:31])[C@H:29]([CH2:32][OH:33])[C@H:28]([OH:34])[C@@H:27]1[OH:35])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:18]([O:25][C@@H:26]1[C@@H:27]([OH:35])[C@@H:28]2[O:34][Si:2]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[O:3][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[O:33][CH2:32][C@H:29]2[C:30]1=[CH2:31])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 1724041,3-DichlorotetraisopropyldisiloxaneHCID 67433587HCID 67433587, compound

Product 1

HCID 67433790HCID 67433790, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (5.5 mL, 16.8 mmol) was added dropwise to a solution of triol 5 (4.0 g, 16.0 mmol) in anhydrous pyridine at −30° C. The reaction mixture was allowed to warm up to room temperature gradually and kept at the same temperature for 2 h. After removing the pyridine in vacuo, the residue was dissolved in EtOAc and washed with H2O and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on a silica gel (EtOAc:Hexanes=1:30 to 1:5) to yield the alcohol 6 (6.5 g, 82%) as a syrup. [α]24D −105.94° (c 0.58, CHCl3); 1H NMR (500 MHz, CDCl3) δ7.41-7.26 (m, 5H), 5.36 (t, J=2.5 Hz, 1H), 5.11 (t, J=2.5 Hz, 1H), 4.77 (d, J=12.0 Hz, 1H), 4.62 (d, J=12.5 Hz, 1H), 4.18-4.14 (m, 2H), 4.05 (dd, J=4.5 and 12.0 Hz, 1H), 3.78 (dd, J=8.0 and 12.0 Hz, 1H), 2.90-2.88 (m, 1H), 1.08-0.97 (m, 27H); 13C NMR (125 MHz, CDCl3) δ 147.3, 138.1, 128.4, 127.6, 127.5, 111.1, 80.2, 74.2, 71.2, 71.1, 64.9, 50.1, 17.6, 17.5, 17.4, 17.3, 17.2, 17.1, 17.0. Anal. Calcd. for C26H44O5Si2: C, 63.37; H, 9.00. Found: C, 63.64; H, 9.05.

Workup

  1. customAfter removing the pyridine in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with H2O and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on a silica gel (EtOAc:Hexanes=1:30 to 1:5)

Sources & evidence

ORD record
ord-a4895564e4fa40088324fe412968479d
Source dataset
uspto-grants-2015_02
Patent number
US08946244B2

Reaction notes

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