2-(3-Bromopropoxy)tetrahydro-2H-pyran → Methyl 3-tert-butyl-5-[3-(tetrahydropyran-2-yloxy)propoxymethyl]benzoate

HRID 657969Notes

Reaction equation

HRID 657969 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1>>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][O:16][CH2:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 12144659Methyl 3-tert-butyl-5-(hydroxymethyl)benzoate

Product 1

HCID 66941442Methyl 3-tert-butyl-5-[3-(tetrahydropyran-2-yloxy)propoxymethyl]benzoate

Procedure

Methyl 3-tert-butyl-5-hydroxymethylbenzoate (3.5 g) was reacted with 2-(3-bromopropoxy)-tetrahydropyran analogously to O5.063 to give methyl 3-tert-butyl-5-[3-(tetrahydropyran-2-yloxy)propoxymethyl]benzoate, and the latter was subsequently converted to the title compound according to the sequence O4.059 to O2.059. 1.75 g of the title compound were obtained.

Sources & evidence

ORD record
ord-a35e34affba6416a9c512c46df1c34d3
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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