Water → 1-Hydroxy-3-methoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-one

HRID 1988220Notes

Reaction equation

HRID 1988220 reaction equation
C[O:2][C:3]1[C:8]2[C:9](=[O:22])[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:7]=2[CH:6]=[C:5]([O:23][CH3:24])[CH:4]=1.[S-]CC.[Na+].O>CN(C)C=O>[OH:2][C:3]1[C:8]2[C:9](=[O:22])[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:7]=2[CH:6]=[C:5]([O:23][CH3:24])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4459711Sodium ethanethiolateHCID 688714241,3-Dimethoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-one

Product 1

HCID 688703781-Hydroxy-3-methoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-oneYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-dimethoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-one (321 mg, 0.96 mmol) and sodium thioethoxide (97 mg, 1.15 mmol) in dimethyl formamide was heated at 140° C. for 4 h whereby it was poured into water (100 ml). Extraction and chromatography gave 1-hydroxy-3-methoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-one (117 mg).

Workup

  1. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-2f17842e16244b2285ba143071b92afb
Source dataset
uspto-grants-2009_06
Patent number
US07553979B2

Reaction notes

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