Ethanol → HCID 58444579, compound

HRID 1509762Notes

Reaction equation

HRID 1509762 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([CH:20]([CH2:23][CH2:24][CH3:25])[CH2:21]O)=[CH2:19].[Bi](Br)(Br)[Br:27].C(O)C>ClCCl.ClCCCC>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]2[CH2:19][CH:18]([Br:27])[CH:20]([CH2:23][CH2:24][CH3:25])[CH2:21][O:14]2)=[CH:11][C:10]=1[F:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 82232bismuth(III) bromideHCID 110838652-Ethenyl-1-pentanolHCID 219768984-(Benzyloxy)-3-fluorobenzaldehyde

Product 1

HCID 58444579HCID 58444579, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8005Butyl ChlorideSolvent

Procedure

188.0 g (0.79 mol) of 4-benzyloxy-3-fluorobenzaldehyde are initially introduced in 1000 ml of dichloromethane at 0° C. together with 90.0 g (0.79 mol) of 2-vinylpentan-1-ol. 176.0 g (0.39 mol) of bismuth(III) bromide are added in portions, and the mixture is stirred at room temperature for 19 h. Insoluble constituents are separated off, and the mixture is filtered absorptively (SiO2, CH2Cl2). The filtrate is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1). The oil obtained is taken up in chlorobutane, and the solution is added dropwise to cold ethanol. The crystals which deposit are collected and recrystallised again from n-heptane. In this way, 2-(4-benzyloxy-3-fluorophenyl)-4-bromo-5-propyltetrahydropyran is obtained as a yellowish solid.

Workup

  1. customInsoluble constituents are separated off
  2. filtrationthe mixture is filtered absorptively (SiO2, CH2Cl2)
  3. concentrationThe filtrate is concentrated to dryness
  4. customthe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1)
  5. customThe oil obtained
  6. customThe crystals which deposit are collected
  7. customrecrystallised again from n-heptane

Sources & evidence

ORD record
ord-066c524e71de4c1c980731f2807f6638
Source dataset
uspto-grants-2012_07
Patent number
US08211513B2

Reaction notes

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