Hydrochloric Acid → HCID 86603001, compound

HRID 2375950Notes

Reaction equation

HRID 2375950 reaction equation
[OH:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C@@H:12]([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:3]([CH3:5])[CH3:4].N1C=CC=CC=1.[C:23]1([P:29](Cl)(Cl)=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>CC(OC)(C)C>[CH:3]([C@H:2]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C@H:12]([CH:13]([CH3:15])[CH3:14])[O:16][P:29](=[O:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:1]1)([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 69990Phenylphosphonic dichlorideHCID 69311580HCID 69311580, compound

Product 1

HCID 86603001HCID 86603001, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of (S)-1-[2-((S)-1-Hydroxy-2-methylpropyl)phenyl]-2-methyl-propan-1-ol (1.0 g, 4.9 mmol) in pyridine (1.16 g 14.7 mmol) was cooled with an ice-bath. To this mixture was then added drop wise phenyl phosphonic acid dichloride (0.96 g, 4.9 mmol). After stirring for 90 minutes the reaction was complete by 31P-NMR. To the mixture was then added TBME (ca. 20 ml) and hydrochloric acid (ca. 5 ml 4N-solution). The organic layer was separated, dried (Na2SO4), and removal of the solvent left the product as an oil. Yield 1.50 g (89%). 1H/13C-NMR (CDCl3, HSQC/HMBC) δ/δ 0.965 (d, J=6.5 Hz)/20.38 (CH3); 1.075 (d, J=6.5 Hz)/19.05 (CH3); 1.106 (d, J=6.5 Hz)/17.71 (CH3); 1.112 (d, J=6.7 Hz)/20.38 (CH3); 2.37 (m)/34.58 (d, J=8.3 Hz) (CHMe2); 2.49 (m)/31.28 (d, J=7.6 Hz) (CHMe2); 5.17 (dd, J=5.6 Hz, J=7.6 Hz)/83.85 (d, J=8.9 Hz) (CH(i-Pr)); 5.53 (dd, J=3.8 Hz, J=5.9 Hz)/84.36 (d, J=7.6 Hz) (CH(i-Pr)); 7.24 (m)/127.28 (Ar CH); 7.24 (m)/127.93 (Ar CH); 7.24 (m)/127.95 (Ar CH); 7.27 (m)/128.31 (Ar CH); 7.37 (m)/128.43 (d, J=15.1 Hz) (Ph meta-CH); 129.12 (d, J=193 Hz) (Ph ipso-C); 7.47 (m)/132.38 (d, J=3.0 Hz) (Ph para-CH); 7.70 (m)/131.63 (d, J=9.8 Hz) (Ph ortho-CH); 137.23 (s), 138.48 (d, J=1.0 Hz) (2 Ar ipso-C). 31P-NMR (CDCl3) δ 18.72.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. custom(Na2SO4), and removal of the solvent
  4. waitleft the product as an oil

Sources & evidence

ORD record
ord-ae8be78013de407cbad114b1b7be47f8
Source dataset
uspto-grants-2008_12
Patent number
US07465838B2

Reaction notes

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