1,5-Dibromopentane → HCID 14329715, compound

HRID 2232497Notes

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>>[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

Reactant 2

HCID 81001,5-Dibromopentane

HCID 10171518HCID 10171518, compound

Product 1

HCID 14329715HCID 14329715, compoundYield 90%

Procedure

Using the procedure and molar proportions of example 71, 1 g of racemic-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 racemic-6-[(5-bromopentyl)oxy]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester as a colorless solid, mp 72.5°-74.5° C. in 90% yield after purification by chromatography on silica gel.

Sources & evidence

ORD record: ord-b30991230e784c6082177813c05a469e
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788214

Reaction notes

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