3-Bromo-1-propanol → HCID 86756214, compound

HRID 565149Notes

Reaction equation

HRID 565149 reaction equation
[OH:1][N:2]=[C:3]([C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1)[C:4]([NH:6][C:7]1[CH:18]=[CH:17][C:10]([C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])=[CH:9][CH:8]=1)=[O:5].Br[CH2:34][CH2:35][CH2:36][OH:37]>>[OH:37][CH:36]([O:1][N:2]=[C:3]([C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1)[C:4]([NH:6][C:7]1[CH:18]=[CH:17][C:10]([C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])=[CH:9][CH:8]=1)=[O:5])[CH2:35][CH3:34]

Participants

3

Reactant 2

HCID 123083-Bromo-1-propanolHCID 73433351HCID 73433351, compound

Product 1

HCID 86756214HCID 86756214, compound

Procedure

Following the basic procedure of Example 1 (f), 3.4 g (7.8 mmol) of allyl 4-[α-hydroxyimino-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoate were reacted with 710 μl (7.8 mmol) of 3-bromo-1-propanol. 1.4 g (36%) of the syn allyl ester and 710 mg (18%) of the trans allyl ester were recovered after purification by chromatography on a silica column, eluted with dichloromethane.

Workup

  1. custom1.4 g (36%) of the syn allyl ester and 710 mg (18%) of the trans allyl ester were recovered
  2. customafter purification by chromatography on a silica column
  3. washeluted with dichloromethane

Sources & evidence

ORD record
ord-edddca9533dc4313a6a2e4f2d7082c9f
Source dataset
uspto-grants-2001_01
Patent number
US06171603B2

Reaction notes

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