m-Chloroperbenzoic acid → HCID 10793277, compound

HRID 2211392Notes

Reaction equation

HRID 2211392 reaction equation
[CH2:1]([C:4]1[C:19]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[C:29]([OH:31])[C:28]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:27][C:26]=2[CH2:39][CH3:40])=[CH:18][CH:17]=[CH:16][C:5]=1[S:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])[CH2:2][CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:46]>C(Cl)Cl>[CH2:1]([C:4]1[C:19]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[C:29]([OH:31])[C:28]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:27][C:26]=2[CH2:39][CH3:40])=[CH:18][CH:17]=[CH:16][C:5]=1[S:6]([C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:46])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9872540HCID 9872540, compound

Product 1

HCID 10793277HCID 10793277, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]thiophenoxy]benzoic acid (450 mg, 0.803 mmol) in methylene chloride (10 mL) at -78° C. was added a solution of 85% m-chloroperoxybenzoic acid (138 mg) in methylene chloride (2 mL). After 40 minutes the mixture was concentrated in vacuo. Purification of the residue via silica gel chromatography (95% chloroform/4.5% methanol/0.5% acetic acid) provided 380 mg (80%) of the title product as an off-white solid: mp >100° C. (dec); NMR (CDCl3) 8.53 (d, J=8 Hz, 1H), 8.14 (d, J=8 Hz, 1H), 7.93 (t, J=8 Hz, 1H), 7.63 (t, J=8 Hz, 1H), 7.43 (m, 2H), 7.13 (m, 2H), 6.94-7.06 (m, 2H), 6.88 (d, J=8 Hz, 1H), 6.50 (d, J=8 Hz, 1H), 7.46 (s, 1H), 6.38 (bs, 1H, --OH), 4.15 (m, 4H), 3.32 (m, 1H), 3.08 (m, 1H), 2.57 (q, J=7.5 Hz, 2H), 2.29 (quintet, J=6 Hz, 2H), 1.75 (m, 2H), 1.17 (t, J=7.5 Hz, 3H), 1.05 (t, J=7.3 Hz, 3H); MS (high resolution) calc 577.202642 (MH+), found 577.203800; IR (CHCl3, cm-1) 2969, 1708, 1497, 1455, 1266, 1146, 1018. Analysis for C33H33O6FS: Calc: C, 68.73; H, 5.77; Found: C, 67.54; H, 5.69.

Workup

  1. concentrationAfter 40 minutes the mixture was concentrated in vacuo
  2. customPurification of the residue via silica gel chromatography (95% chloroform/4.5% methanol/0.5% acetic acid)

Sources & evidence

ORD record
ord-d4d182c7be38421f90702db7295bd5ca
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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