Water → HCID 68869093, compound

HRID 1988222Notes

Reaction equation

HRID 1988222 reaction equation
C[O:2][C:3]1[C:8]2[C:9](=[O:20])[O:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][O:19][C:7]=2[CH:6]=[C:5]([O:21][CH3:22])[CH:4]=1.[S-]CC.[Na+].O>CN(C)C=O>[OH:2][C:3]1[C:8]2[C:9](=[O:20])[O:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][O:19][C:7]=2[CH:6]=[C:5]([O:21][CH3:22])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4459711Sodium ethanethiolateHCID 68868897HCID 68868897, compound

Product 1

HCID 68869093HCID 68869093, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-dimethoxy-6,7,8,11,12,13-hexahydro-5,14-dioxa-benzocyclotridecen-15-one (95 mg, 0.30 mmol) and sodium thioethoxide (31 mg, 0.37 mmol) in dimethyl formamide was heated at 140° C. for 4 h whereby it was poored into water (100 ml). Extraction and chromatography gave 1-hydroxy-3-methoxy-6,7,8,11,12,13-hexahydro-5,14-dioxa-benzocyclotridecen-15-one (20 mg).

Workup

  1. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-289e422883764ef39f297f8d2dbdd5d7
Source dataset
uspto-grants-2009_06
Patent number
US07553979B2

Reaction notes

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