Pentane → 5-Ethyl-4-[(4-methoxyphenyl)sulfonyl]-2-vinyl4,5-dihydrothieno[3,2-c]isoquinoline

HRID 641633Notes

Reaction equation

HRID 641633 reaction equation
[CH3:1]CCCC.C([Li])(C)(C)C.[CH2:11]([CH:13]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[S:23][C:24]([CH:26]=O)=[CH:25][C:15]=2[N:14]1[S:28]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH3:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:11]([CH:13]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[S:23][C:24]([CH:26]=[CH2:1])=[CH:25][C:15]=2[N:14]1[S:28]([C:31]1[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=1)(=[O:29])=[O:30])[CH3:12]

Participants

6

Reactant 3

HCID 8003PentaneHCID 58669398HCID 58669398, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 586693955-Ethyl-4-[(4-methoxyphenyl)sulfonyl]-2-vinyl4,5-dihydrothieno[3,2-c]isoquinolineYield 90%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

A suspension of methyltriphenylphosphonium bromide (2.30 g, 6.44 mmol) in dry tetrahydrofuran (16 mL) was treated dropwise with a pentane solution of t-butyllithium (1.0 M, 3.9 mL, 3.9 mmol) at 0° C. during several min. After the addition was complete, the suspension was warmed to 23° C. and after a further 10 min, a solution of 5-ethyl-4-[(4-methoxyphenyl)sulfonyl]-4,5-dihydrothieno[3,2-c]isoquinoline-2-carbaldehyde (1.33 g, 3.22 mmol) in dry tetrahydrofuran (16 mL+8 mL wash) was added. After a further 15 min, the reaction was quenched with water (160 mL) and extracted with ethyl acetate (160 mL). The extract was washed with brine (160 mL), dried (Na2SO4), and concentrated in vacuo to give the crude product as an orange solid (2.46 g). Flash chromatography on silica gel (24 g) eluting 25-, and then 50% methylene chloride-hexane gave the title compound (1.20 g, 90%, m.p. 131-33° C.) as a pale yellow solid.

Workup

  1. additionAfter the addition
  2. customthe reaction was quenched with water (160 mL)
  3. extractionextracted with ethyl acetate (160 mL)
  4. washThe extract was washed with brine (160 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give the crude product as an orange solid (2.46 g)
  8. washFlash chromatography on silica gel (24 g) eluting 25-

Sources & evidence

ORD record
ord-8406db38cbc24489a0f8c5bffdfe14b2
Source dataset
uspto-grants-2010_04
Patent number
US07696221B2

Reaction notes

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