Acetonitrile--water (1/1) → HCID 86750303, compound

HRID 1450035Notes

Reaction equation

HRID 1450035 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([CH2:12][S:13][C:14]1[C:25]2[O:24][C:23]([CH3:27])([CH3:26])[O:22][C:21]=2[C:20]([C:28]([C:53]2[C:63]3[O:64][C:65]([CH3:68])([CH3:67])[O:66][C:62]=3[C:61]([S:69][CH2:70][C:71](OCC)=[O:72])=[C:55]3[O:56][C:57]([CH3:60])([CH3:59])[O:58][C:54]=23)([C:30]2[C:40]3[O:41][C:42]([CH3:45])([CH3:44])[O:43][C:39]=3[C:38]([S:46][CH2:47][C:48](OCC)=[O:49])=[C:32]3[O:33][C:34]([CH3:37])([CH3:36])[O:35][C:31]=23)[OH:29])=[C:19]2[C:15]=1[O:16][C:17]([CH3:77])([CH3:76])[O:18]2)=O)C.C(#N)C.O>C(OCC)C.C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC>[OH:9][CH2:10][CH2:12][S:13][C:14]1[C:15]2[O:16][C:17]([CH3:76])([CH3:77])[O:18][C:19]=2[C:20]([C:28]([C:30]2[C:40]3[O:41][C:42]([CH3:45])([CH3:44])[O:43][C:39]=3[C:38]([S:46][CH2:47][CH2:48][OH:49])=[C:32]3[O:33][C:34]([CH3:36])([CH3:37])[O:35][C:31]=23)([C:53]2[C:63]3[O:64][C:65]([CH3:67])([CH3:68])[O:66][C:62]=3[C:61]([S:69][CH2:70][CH2:71][OH:72])=[C:55]3[O:56][C:57]([CH3:59])([CH3:60])[O:58][C:54]=23)[OH:29])=[C:21]2[C:25]=1[O:24][C:23]([CH3:27])([CH3:26])[O:22]2

Participants

6

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 21226445Aluminium lithium hydrideHCID 86750304HCID 86750304, compound

Product 1

HCID 86750303HCID 86750303, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 82707Tetrabutylammonium AcetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

LiAlH4 (15.2 mg, 0.40 mmol) was added to a solution of tris(8-ethoxycarbonylmethylthio-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methanol (10.5 mg 0.10 mmol (Example 27)) in diethyl ether (10 mL) under nitrogen at 20° C. The reaction was followed by HPLC (reversed phase C18, acetonitrile:water (3:1), 5 mM tetrabutylammonium acetate). The mixture was quenched with ethylacetate when no more substrate was seen by HPLC. Dilute sulfuric acid was then added until pH 6-7. The ether phase was separated, and the water phase was extracted with diethyl ether. The combined etheric phases were dried (MgSO4) and evaporated, yielding 0.0901 g (97.8%, 0.0978 mmol) of a yellowish oil, which gradually crystallized upon standing.

Workup

  1. customThe mixture was quenched with ethylacetate when no more substrate
  2. additionDilute sulfuric acid was then added until pH 6-7
  3. customThe ether phase was separated
  4. extractionthe water phase was extracted with diethyl ether
  5. dry with materialThe combined etheric phases were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0d0300ed9af8429396ac3502b253a244
Source dataset
uspto-grants-1997_02
Patent number
US05599522

Reaction notes

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