Quinoline → HCID 70619032, compound

HRID 616864Notes

Reaction equation

HRID 616864 reaction equation
[OH:1][C@H:2]([C:26]#[C:27][CH3:28])[CH2:3][C@:4]1([CH3:25])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH3:24])[C:8]([CH3:23])=[C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[CH3:14])[O:5]1.N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C.CCCCCC>[OH:1][C@H:2](/[CH:26]=[CH:27]\[CH3:28])[CH2:3][C@:4]1([CH3:25])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH3:24])[C:8]([CH3:23])=[C:9]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:10]=2[CH3:14])[O:5]1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 22796790HCID 22796790, compound

Product 1

HCID 70619032HCID 70619032, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

2.5 g. of 2(S)-[2(S)-hydroxy-3-pentynyl]-2,5,7,8-tetramethyl-6-benzyloxychroman and 0.25 g. of Lindlar catalyst in 15 ml. of ethyl acetate-hexane (2 = 1 parts by volume) containing 0.1 ml. of quinoline was hydrogenated at 25° C. and atmospheric pressure. The catalyst was filtered off and washed with ethyl acetate. The ethyl acetate solution was washed with 1.0 N aqueous HCl (3 × 50 ml.), dried over MgSO4 and concentrated in vacuo to give 2.508 g. of crude product. Crystallization of this material from pentane yield 2.053 g. of 2(S)-[2(S)-hydroxy-3(Z)-pentenyl]-2,5,7,8-tetramethyl-6-benzyloxychroman as white crystalls, m.p. 84°-86° C. [α]D25 - 30.57° (CHCl3).

Workup

  1. customwas hydrogenated at 25° C.
  2. filtrationThe catalyst was filtered off
  3. washwashed with ethyl acetate
  4. washThe ethyl acetate solution was washed with 1.0 N aqueous HCl (3 × 50 ml.)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give 2.508 g
  8. customCrystallization of this material from pentane yield 2.053 g

Sources & evidence

ORD record
ord-045b20cf4a5444b3a4897eb4b4259e17
Source dataset
uspto-grants-1978_02
Patent number
US04076739

Reaction notes

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