Water → HCID 66730386, compound

HRID 85004Notes

Reaction equation

HRID 85004 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][P:28](=[O:35])([O:32]CC)[O:29]CC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[Si](C)(C)C.O>ClCCl.CO>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][P:28](=[O:29])([OH:32])[OH:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 86664728HCID 86664728, compound

Product 1

HCID 66730386HCID 66730386, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl 10-(8-(benzyloxy)octyloxy)decylphosphonate (680 mg, 1.33 mmol) was dissolved in dry dichloromethane (15 mL). Bromotrimethylsilane (0.53 mL, 4.05 mmol) was added via syringe. The reaction was capped with a greased glass stopper and stirred overnight. The volatiles were removed under reduced pressure to yield a yellow oil. This was dissolved in 5:1 methanol:water (10 mL) and stirred 4 hours more. After concentration of the organic, the viscous yellow oil was recrystallized in acetonitrile to yield a white crystalline solid (590 mg, 98% yield). 1H NMR (400.14 MHz, DMSO) δ 7.40-7.19 (m, 5H), 4.42 (2H), 3.39 (t, J=6.48 Hz, 2H), 3.29 (t, J=6.46 Hz, 4H), 1.58-1.34 (m, 10H), 1.34-1.10 (m, 20H). 13C{1H} NMR (100.62 MHz, DMSO) δ 138.7, 128.2 (2C), 127.3 (2C), 127.3, 71.79, 69.91 (2C), 69.59, 30.11 (d, J=16.0 Hz), 29.25, 29.21, 29.20, 29.05, 28.89 (2C), 28.84 (2C), 28.73, 27.55 (d, J=136.5 Hz), 25.76, 25.69, 25.67, 22.74 (d, J=4.5 Hz). 31P{1H} NMR (161.97 MHz, DMSO): δ 27.74. Analysis calculated (found) %: C 65.76 (65.79), H 9.93 (10.00). MS (ESI, m/z): 455 (M−, 100%). Exact mass calculated (found) for [M−H]−, m/z): 455.2932 (455.2932).

Workup

  1. customThe reaction was capped with a greased glass stopper
  2. customThe volatiles were removed under reduced pressure
  3. customto yield a yellow oil
  4. customAfter concentration of the organic, the viscous yellow oil was recrystallized in acetonitrile

Sources & evidence

ORD record
ord-752d61f66b99418d9171ebde5188ab13
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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