Phosphate → HCID 20073356, compound

HRID 704810Notes

Reaction equation

HRID 704810 reaction equation
[Cl:1][CH2:2][C:3]([O:5][CH:6]([CH3:22])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)=[O:4].P([O-])([O-])([O-])=O.[OH-].[Na+]>C(Cl)Cl>[O:15]([C:11]1[CH:10]=[C:9](/[CH:8]=[CH:7]/[CH:6]([OH:5])[CH3:22])[CH:14]=[CH:13][CH:12]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1.[Cl:1][CH2:2][C:3]([O:5][CH:6]([CH3:22])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 14798Sodium HydroxideHCID 20073365(E)-1-(3-phenoxyphenyl)but-1-en-3-yl chloroacetate

Product 2

HCID 20073356HCID 20073356, compoundHCID 20073365(E)-1-(3-phenoxyphenyl)but-1-en-3-yl chloroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (c) (9.5 g) was taken up in 0.1 M aqu. phosphate buffer (250 ml, pH 7) under N2 and lipase (150 mg, Fluka Cat. No. 62312) was added. As the reaction proceeded, 1 M aqu. NaOH was added from an autoburette to maintain the pH at 7 (14.5 ml added over 27 hours). After 27 hours, methylene chloride (250 ml) was added, the mixture dried over MgSO4 and stripped, and the residue eluted through a silica gel column using ether. The eluate was monitored by TLC and similar fractions combined and stripped to give (+)-(E)-1-(3-phenoxyphenyl) but-1-en-3-ol (3.7 g, [α]D20 +8.47° (c.2.72, EtOH)) and chiral (E)-1-(3-phenoxyphenyl)but-1-en-3-yl chloroacetate (3.7 g). The latter compound was taken up in methanol (50 ml), anhy. potassium carbonate (1 g) was added, and the mixture stirred for 1/2 hour. The mixture was then stripped, the residue partitioned between ether and water, and the organic phase separated, washed with satd. aqu. NaCl, and stripped to give (-)-(E)-1-(3-phenoxyphenyl)but-1-en-3-ol (2.7 g. [α]D20 -11.0° (c.2.92, EtOH)).

Workup

  1. addition62312) was added
  2. temperatureto maintain the pH
  3. additionat 7 (14.5 ml added over 27 hours)
  4. dry with materialthe mixture dried over MgSO4
  5. washthe residue eluted through a silica gel column

Sources & evidence

ORD record
ord-ad3cd4d02cdd44538eaca84fd947797d
Source dataset
uspto-grants-1991_01
Patent number
US04988733

Reaction notes

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