3,4-dihydro-2H-pyran → HCID 57969203, compound

HRID 1664358Notes

Reaction equation

HRID 1664358 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][N:8]=2)=[CH:4][C:3]=1[CH2:17][OH:18].[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(Cl)Cl>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][N:8]=2)=[CH:4][C:3]=1[CH2:17][O:18][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:19]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 57969172HCID 57969172, compound

Product 1

HCID 57969203HCID 57969203, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

THP protection of 6-(4-bromo-3-(hydroxymethyl)phenoxy)nicotinaldehyde (2.4 g, 7.78 mmol) with 3,4-dihydro-2H-pyran (2.2 mL) catalyzed with (1S)-(+)-10-camphorsulfonic acid in CH2Cl2 (80 mL) at r.t. for 1 h provided the desired 6-(4-bromo-3-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)nicotinaldehyde as colorless oil (3.07 g, 7.8 mmol, yield 100%) after silica gel column purification (hexane:EtOAc=3:1, v/v).

Sources & evidence

ORD record
ord-700d943b0d3a4766885e770868000350
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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