1,5-Dibromopentane → HCID 14329717, compound

HRID 2231919Notes

Reaction equation

HRID 2231919 reaction equation
[CH3:1][O:2][C:3]([C@:5]1([CH3:19])[CH2:10][CH2:9][C:8]2[C:11]([CH3:18])=[C:12]([OH:17])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1)=[O:4].[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C@:5]1([CH3:19])[CH2:10][CH2:9][C:8]2[C:11]([CH3:18])=[C:12]([O:17][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][Br:20])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1)=[O:4]

Participants

4

Reactant 2

HCID 81001,5-DibromopentaneHCID 14308592(S)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester

Product 1

HCID 14329717HCID 14329717, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure and molar proportions of example 71, (S)-(-)-6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester was alkylated with 1,5-dibromopentane giving (S)-(-)-6-[(5-bromopentyl)oxy]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester, [α]D25 -34.60° (c2, CHCl3), in 88.5% yield.

Sources & evidence

ORD record
ord-62b4488e65854bbb993ddc20aca3e499
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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