Trifluoroacetic acid → 3-[5-(Diethoxy-phosphoryl)-thiophen-2-ylmethyl]-5-isopropoxy-benzoic acid

HRID 1431007Notes

Reaction equation

HRID 1431007 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[S:13][C:12]([CH:14](O)[C:15]2[CH:16]=[C:17]([CH:21]=[C:22]([O:24][CH:25]([CH3:27])[CH3:26])[CH:23]=2)[C:18]([OH:20])=[O:19])=[CH:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][P:4]([C:9]1[S:13][C:12]([CH2:14][C:15]2[CH:16]=[C:17]([CH:21]=[C:22]([O:24][CH:25]([CH3:27])[CH3:26])[CH:23]=2)[C:18]([OH:20])=[O:19])=[CH:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 866595583-{[5-(Diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid

Product 1

HCID 866595593-[5-(Diethoxy-phosphoryl)-thiophen-2-ylmethyl]-5-isopropoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{[5-(diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid (700 mg, 1.64 mmol) in CH2Cl2 (10 ml) was added TFA (1.1 ml), followed by triethylsilane (0.92 ml, 5.72 mmol). The reaction mixture was then stirred at r.t. for 30 min, concentrated down, re-dissolved in water, extracted with EtOAc. The EtOAc layer was separated, dried over MgSO4, filtrated, and concentrated to afford the crude product 3-[5-(diethoxy-phosphoryl)-thiophen-2-ylmethyl]-5-isopropoxy-benzoic acid.

Workup

  1. concentrationconcentrated down
  2. dissolutionre-dissolved in water
  3. extractionextracted with EtOAc
  4. customThe EtOAc layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fe276c9087c2475f82aa1648aed7fea4
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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