3-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman → 2-[trans-4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylmethoxy]-ethanol

HRID 564317Notes

Reaction equation

HRID 564317 reaction equation
C([O:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH:22]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:21]2[C:16](=[C:17]([F:34])[CH:18]=[CH:19][C:20]=2[F:33])[O:15][CH2:14]1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([S:23]([C@@H:22]2[C:21]3[C:16](=[C:17]([F:34])[CH:18]=[CH:19][C:20]=3[F:33])[O:15][CH2:14][C@H:13]2[CH2:12][O:11][CH2:10][CH2:9][OH:8])(=[O:24])=[O:25])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 670069033-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chromanHCID 178418361HCID 178418361, compound

Product 1

HCID 589504982-[trans-4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylmethoxy]-ethanol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman (0.4 g, 0.79 mmole) was dissolved in 10 ml EtOAc and Pd(OH)2 was added. Hydrogen was introduced via a balloon. The reaction was stirred at room temperature for 30 minutes. The catalyst was filtered and residue was used in next step without purification. Yield: 0.32 g, 97%. 1H NMR (CDCl3 400 MHz δ 7.73 (d, J=8.1 Hz, 2H), 7.51 (d, J=8.1 Hz, 2H), 7.03 (m, 1H), 6.41 (m, 1H), 4.90 (dd, J=8.8 and 2.9 Hz, 1H), 4.57 (s, 1H), 4.39 (td, J=11.7 and 1.5 Hz, 1H), 3.68 (br, 2H), 3.41-3.54 (m, 3H), 2.30 (t, J=9.5 Hz, 1H), 3.15 (m, 1H).

Workup

  1. filtrationThe catalyst was filtered
  2. customresidue was used in next step without purification

Sources & evidence

ORD record
ord-db686cb3462640a68f844570e8195a1f
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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