Acetic Acid → HCID 10364955, compound

HRID 1689738Notes

Reaction equation

HRID 1689738 reaction equation
[Na].C([C@H:10]([CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:11][CH2:12][P:13]([O:18][CH2:19]C)(=[O:17])[O:14][CH2:15]C)(=O)C1C=CC=CC=1.CC(O)=[O:41]>CO>[CH2:23]([O:22][CH2:21][C@@H:10]([OH:41])[CH2:11][CH2:12][P:13]([O:18][CH3:19])(=[O:17])[O:14][CH3:15])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545Sodium2×HCID 86627329HCID 86627329, compound

Product 1

HCID 10364955HCID 10364955, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 100 mL of dry MeOH was added 0.18 g (7.83 mmol) of sodium metal. After the sodium metal had completely disappeared, a solution of 3.91 g (7.05 mmol) of benzoyl phosphonate 5 in 10 mL of dry MeOH was added. After the mixture was stirred overnight, the reaction was quenched by addition of 500 μL (8.73 mmol) of AcOH and then concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (elution with CHCl3/MeOH 10:1) to provide 2.56 g (86%) of hydroxy phosphonate 6 as a colorless oil; [α]25D −5.20° (c 5.0, C6H6); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=6.8 Hz), 1.26 (br s, 26H), 1.54-1.58 (m, 2H), 1.70-1.90 (m, 4H), 2.78 (br s, 1H), 3.29 (dd, 1H, J=7.1, 9.4 Hz), 3.40-3.48 (m, 3H), 3.74 (d, 6H, J=10.8 Hz), 3.70-3.85 (m, 1H); 13C NMR (CDCl3) δ 14.0, 20.7 (d, J=142.1 Hz), 22.6, 26.0, 26.1 (d, J=4.7 Hz), 29.3, 29.4, 29.5, 29.6, 31.9, 52.3, 69.8 (d, J=14.8 Hz), 71.6, 74.4; MS (electrospray) MH+ m/z calcd for C22H48O5P 423.3, found 423.3.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a residue
  3. customThe residue was purified by column chromatography on silica gel (elution with CHCl3/MeOH 10:1)

Sources & evidence

ORD record
ord-249d3ac24f92462b952a398fa135929f
Source dataset
uspto-grants-2012_04
Patent number
US08153615B2

Reaction notes

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