Triphenylphosphine → HCID 22280037, compound

HRID 1591565Notes

Reaction equation

HRID 1591565 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)=[CH:19][CH:18]=2)=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2.ClC1C=C(CO)C=C(Cl)C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:32][C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([Cl:31])[CH:28]=1)[CH2:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][S:15][C:12]2[CH:13]=[CH:14][C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])=[C:7]3[C:11]=2[CH2:10][CH2:9][CH2:8]3)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 432363,5-Dichlorobenzylic alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20827082HCID 20827082, compound2×

Product 1

HCID 22280037HCID 22280037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation of {7-[4(3,5-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 77A) The product from Example 75C (0.42 g, 1 mmoles), (3,5-dichlorophenyl)-methanol (0.24 g, 1.3 mmoles), triphenyl phosphine (0.38 g, 1.5 mmoles) and 0.23 mL of diethyl azodicarboxylate (0.25 g, 1.5 mmoles) were dissolved in 9 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature under nitrogen for 18 hrs. The reaction mixture was evaporated to give a residue, which was flash chromatographed (silica gel, 20% ethyl acetate in hexane) to afford the title compound in good purity. MS m/z 265 Step 2. Preparation of {7-[4-(3,5-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 77) The title compound was prepared in the manner analogous to Example 1 using 77A. mp 134-135° C.; IR (KBr) cm−1: 3070, 1747, 1708, 1572, 1432, 1244; 400 MHz 1H NMR (DMSO-d6): δ 12.95 (br(s), 1H), 7.51-7.53 (m, 1H), 7.42-7.45 (m, 2H), 7.07-7.13 (m, 2H), 7.04 (d, 1H, J=8.6 Hz), 6.83-6.90 (m, 2H), 6.56 (d, 1H, J=8.6 Hz), 5.05 (s, 2H), 4.61 (s, 2H), 3.93 (s, 2H), 2.75 (t, 2H, J=7.5 Hz), 2.66 (t, 2H, 7.5 Hz), 1.88 (pentet, 2H); MS m/z 487 (M−1). Anal. Calc'd for C25H22Cl2O4S: C, 61.35; H, 4.53; found: C, 61.01; H, 436.

Workup

  1. customThe reaction mixture was evaporated
  2. customto give a residue, which
  3. customchromatographed (silica gel, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ba568f3dbfa644709209cf972beb2218
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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