Hydrochloric Acid → HCID 86603000, compound

HRID 2375949Notes

Reaction equation

HRID 2375949 reaction equation
[OH:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:11]([OH:14])[CH2:12][CH3:13])[CH2:3][CH3:4].N1C=CC=CC=1.[C:21]1([P:27](Cl)(Cl)=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>CC(OC)(C)C>[CH2:3]([C@H:2]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C@H:11]([CH2:12][CH3:13])[O:14][P:27](=[O:28])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:1]1)[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 69990Phenylphosphonic dichlorideHCID 11401308HCID 11401308, compound

Product 1

HCID 86603000HCID 86603000, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of (R,S)-1-[2-(1-Hydroxy-propyl)-phenyl]-propan-1-ol (4.0 g, 20.6 mmol) in pyridine (4.89 g, 61.7 mmol) was cooled with an ice-bath. Then phenyl phosphonic acid dichloride (4.03 g, 20.6 mmol) was added drop wise. The mixture was allowed to warm to ambient temperature, and stirred over night. To the mixture was then added HCl (ca. 20 ml 4N solution) and TBME (ca. 50 ml). The organic layer was separated, dried (sodium sulfate), and after removal of the solvent the product remained as a colourless oil. Yield: 5.88 g (90.3%). 1H/13C-NMR (CDCl3, HSQC/HMBC) δ/δ 1.05 (tr, J=7.4 Hz)/11.05 (CH3); 1.13 (tr, J=7.6 Hz)/10.48 (CH3); 2.05-2.21 (m)/27.82 (d, J=8.9 Hz), 30.61 (d, J=9.4 Hz) (2 CH2Me); 5.42 (ddd, J=4.7 Hz, J=5.8 Hz, J=8.5 Hz)/80.30 (d, J=7.6 Hz) (CHEt); 5.75 (ddd, J=3.8 Hz, J=5.3 Hz, J=7.4 Hz)/80.47 (d, J=7.3 Hz) (CHEt); 7.24/126.73 (Ar CH); 7.24/127.18 (Ar CH); 7.24/128.12 (Ar CH); 7.31/128.59 (Ar CH); 7.40/128.47 (d, J=15.2 Hz) (Ph meta-CH); 128.93 (d, J=192 Hz) (Ph ipso-C); 7.51/132.47 (d, J=3.1 Hz) (Ph para-CH); 7.73/131.74 (d, J=9.8 Hz) (Ph ortho-CH); 137.66, 138.92 (2 Ar ipso-C). 31P-NMR (CDCl3) δ 19.26.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (sodium sulfate)
  3. customafter removal of the solvent the product

Sources & evidence

ORD record
ord-a55a19bb251a4eba938d7a08fe7cb239
Source dataset
uspto-grants-2008_12
Patent number
US07465838B2

Reaction notes

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