HCID 12802895, compound → HCID 70431127, compound

HRID 354569Notes

Reaction equation

HRID 354569 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1/[CH:17]=[CH:18]/[C@@H:19]1[O:24][C:23](=[O:25])[CH2:22][C@@H:21]([OH:26])[CH2:20]1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]=1[CH2:17][CH2:18][C@@H:19]1[O:24][C:23](=[O:25])[CH2:22][C@@H:21]([OH:26])[CH2:20]1

Participants

3

Reactant 1

HCID 12802895HCID 12802895, compound

Product 1

HCID 70431127HCID 70431127, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-(E)-6-[2-(2,4-dichloro-6-phenylmethoxyphenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1.1 g, 28 mmole) in tetrahydrofuran (50 ml) was magnetically stirred and hydrogenated at room temperature and atmospheric pressure in the presence of 110 mg of 5% rhodium on carbon catalyst until 1.5 molar equivalents of hydrogen had been consumed. After removing the catalyst by filtration, the filtrate was evaporated in vacuo leaving the title compound as a pale yellow oil. The oil was chromatographed on a silica gel column (200 g). Elution with acetone-methylene chloride (1:9, v:v; 560 ml) provided a forerun which was discarded. Continued elution with the same eluant (240 ml) gave the title compound as a colorless oil which solidified when it was triturated with ether. The title compound was purified by recrystallization from ether-hexane (1:1, v:v; 20 ml) to give colorless needles (0.67 g, 61%) melting at 99°-101° C.: pmr (CDCl3) δ1.83 (4 H, m), 2.60 (2H, m), 2.90 (2H, m), 4.30 (H, m), 4.62 (H, m), 5.05 (2H, s), 7.42 (5H, s).

Workup

  1. customhydrogenated at room temperature
  2. customatmospheric pressure in the presence of 110 mg of 5% rhodium on carbon catalyst until 1.5 molar equivalents of hydrogen had been consumed
  3. customAfter removing the catalyst
  4. filtrationby filtration
  5. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-3733685c1d884ae0af1c641f91390dd5
Source dataset
uspto-grants-1983_03
Patent number
US04375475

Reaction notes

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