HCID 20040847, compound → HCID 20040849, compound

HRID 1762452Notes

Reaction equation

HRID 1762452 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([S:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH:25]2[C:34]3[C:29](=[CH:30][C:31]([OH:35])=[CH:32][CH:33]=3)[CH2:28][CH2:27][C:26]2([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[CH3:36])[CH:20]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>O.CO.O1CCCC1>[CH2:7]([S:13]([CH2:14][CH2:15][C:16]1[CH:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH:25]2[C:34]3[C:29](=[CH:30][C:31]([OH:35])=[CH:32][CH:33]=3)[CH2:28][CH2:27][C:26]2([C:37]2[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=2)[CH3:36])[CH:20]=1)=[O:2])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 2

HCID 20040847HCID 20040847, compoundHCID 23667635Sodium periodate

Product 1

HCID 20040849HCID 20040849, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium metaperiodate (0.1 g.) in water (2 ml.) was added to a stirred solution of (1RS,2RS)-1-{4-[4-(2-hexylthioethyl)pyrazol-1-yl]butyl}-1,2,3,4-tetrahydro-2-p-hydroxyphenyl-2-methylnaphth-6-ol (Example 1; 0.23 g.) in a mixture of methanol (4 ml.) and tetrahydrofuran (4 ml.) and the mixture was stirred at laboratory temperature for 16 hours, diluted with water (20 ml.) and extracted three times with methylene chloride (10 ml. each time). The combined extracts were dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 49:1 v/v mixture of ethyl acetate and ethanol as eluent. There was thus obtained as an oil (1RS,2RS)-1-{4-[4-(2-hexylsulphinylethyl)pyrazol-1-yl]butyl}-1,2,3,4-tetrahydro-2-p-hydroxyphenyl-2-methylnaphth-6-ol.

Workup

  1. extractionextracted three times with methylene chloride (10 ml
  2. customThe combined extracts were dried
  3. customevaporated to dryness
  4. customthe residue was purified by chromatography on a silica gel column
  5. additiona 49:1 v/v mixture of ethyl acetate and ethanol as eluent

Sources & evidence

ORD record
ord-bce07b9022e94ae58940f347ea30877a
Source dataset
uspto-grants-1989_05
Patent number
US04833135

Reaction notes

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