Trimethyl phosphite → HCID 13614887, compound

HRID 1482770Notes

Reaction equation

HRID 1482770 reaction equation
Br[CH2:2][C:3](=[O:15])[C:4]([CH3:14])([O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])[CH3:5].[P:16]([O:21]C)([O:19][CH3:20])[O:17][CH3:18]>C1(C)C=CC=CC=1>[CH3:18][O:17][P:16]([CH2:2][C:3](=[O:15])[C:4]([CH3:14])([O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])[CH3:5])([O:19][CH3:20])=[O:21]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 90282915HCID 90282915, compound

Product 1

HCID 13614887HCID 13614887, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 14 (1.55 g; 5.25 mmol) and trimethyl phosphite (514 μl; 782 mg; 6.31 mmol) in toluene (20 ml) was refluxed for 3 days. The mixture was purified by column chromatography (5-15% 2-propanol/hexane) to give 1.54 g (4.75 mmol; 90% yield) of 2. 1H NMR (400 MHz, CDCl3) δ 0.65 (6H, q, J=7.9 Hz), 0.98 (9H, t, J=7.9 Hz), 1.36 (6H, s), 3.40 (2H, d, JH—P=20.7 Hz) 3.80 (6H, d, JH—P=11.2 Hz); 13C NMR (101 MHz, CDCl3) δ 6.4, 6.9, 26.8, 33.7 (d, JC—P=137.8 Hz), 52.8 (d, JC—P=6.7 Hz) 80.0, 207.1 (d, JC—P=6.0 Hz); MS (EI) m/z 324 ([M−Et]+, 98), 238 (65), 211 (61), 173 (100); exact mass calculated for C11H24O5PSi ([M−Et]+) 295.1126. found 295.1126.

Workup

  1. customThe mixture was purified by column chromatography (5-15% 2-propanol/hexane)
  2. customto give 1.54 g (4.75 mmol; 90% yield) of 2

Sources & evidence

ORD record
ord-e7ea03e7cc494af8ba64b8a2054931dc
Source dataset
uspto-grants-2016_08
Patent number
US09416102B2

Reaction notes

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