Tetrahydrofuran → HCID 10363633, compound

HRID 970843Notes

Reaction equation

HRID 970843 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][C:14]2[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20](OCC)=[O:21])=[C:16]([CH2:27][CH3:28])[CH:15]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][OH:10].[CH2:29]([Mg]Br)[CH3:30].[Cl-].[NH4+].[CH2:35]1COC[CH2:36]1>>[CH2:27]([C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([CH2:9][OH:10])=[C:3]([CH2:2][OH:1])[CH:4]=2)[CH:26]=[CH:25][C:17]=1[O:18][CH2:19][C:20]([CH2:29][CH3:30])([OH:21])[CH2:35][CH3:36])[CH3:28]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86600275HCID 86600275, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 10363633HCID 10363633, compound

Procedure

640 mg (1.65 mmol) of ethyl {4-[3-(3,4-bis-hydroxymethyl-phenyl)-propyl]-2-ethyl-phenoxy}-acetate are dissolved in 30 ml of THF. 2.2 ml (6.6 mmol) of a 3M ethylmagnesium bromide solution are added dropwise. The reaction medium is stirred for 30 minutes, and is then treated with a saturated ammonium chloride solution. The residue obtained after extraction and concentration is purified by chromatography on a silica column. A colorless oil is obtained (m=510 mg, y=77%).

Workup

  1. customThe residue obtained
  2. extractionafter extraction and concentration
  3. customis purified by chromatography on a silica column
  4. customA colorless oil is obtained (m=510 mg, y=77%)

Sources & evidence

ORD record
ord-dece87126346403095e39a22be16ce75
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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