Sulfuric Acid → HCID 131710140, compound

HRID 1283370Notes

Reaction equation

HRID 1283370 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][C@H:9]1[O:14][C@@H:13]([O:15][C@@H:16]2[CH2:32][C@:31]3([OH:33])[C@@:19]([CH:42]=[O:43])([C@@H:20]4[C@@H:28]([CH2:29][CH2:30]3)[C@:27]3([OH:34])[C@@:23]([CH3:41])([C@@H:24]([C:35]5[CH2:40][O:39][C:37](=[O:38])[CH:36]=5)[CH2:25][CH2:26]3)[CH2:22][CH2:21]4)[CH2:18][CH2:17]2)[CH2:12][C@H:11]([OH:44])[C@@H:10]1[OH:45].[BH4-].[Na+].S(=O)(=O)(O)O>O1CCOCC1>[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][CH:9]1[O:14][CH:13]([O:15][CH:16]2[CH2:32][C:31]3([OH:33])[C:19]([CH2:42][OH:43])([CH:20]4[CH:28]([CH2:29][CH2:30]3)[C:27]3([OH:34])[C:23]([CH3:41])([CH:24]([C:35]5[CH2:40][O:39][C:37](=[O:38])[CH:36]=5)[CH2:25][CH2:26]3)[CH2:22][CH2:21]4)[CH2:18][CH2:17]2)[CH2:12][CH:11]([OH:44])[CH:10]1[OH:45]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 131710139HCID 131710139, compound2×

Product 1

HCID 131710140HCID 131710140, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1.5 g. cyclohexanone-helveticoside are dissolved in 20 ml. of 80% aqueous dioxane and treated dropwise over a period of 1 hour with a solution of 0.35 g. sodium borohydride in 20 ml. of 75% dioxane. The reaction mixture is stirred for 1 hour, after which no more cyclohexanone-helveticoside can be detected. The solution is adjusted to pH 7 with dilute sulfuric acid, and the dioxane is evaporated under reduced pressure in a rotating evaporator. The aqueous phase is extracted repeatedly with chloroform. The combined chloroform extracts are dried over anhydrous sodium sulfate and evaporated. The residue is purified chromatographically over silica gel, using chloroform as solvent. Yield: 750 mg. cyclohexanone-helveticosol. Melting point: 155°-164°C;[αD20 ] (C = 1, chloroform) : +23°.

Workup

  1. customthe dioxane is evaporated under reduced pressure in a rotating evaporator
  2. extractionThe aqueous phase is extracted repeatedly with chloroform
  3. dry with materialThe combined chloroform extracts are dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue is purified chromatographically over silica gel
  6. custom+23°

Sources & evidence

ORD record
ord-bf3a5a81dddf4741a30eb69d581c6c1e
Source dataset
uspto-grants-1976_08
Patent number
US03975373

Reaction notes

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