Water → HCID 22827413, compound

HRID 358360Notes

Reaction equation

HRID 358360 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][C@@H:18]([CH2:37][C:38]#[C:39][CH2:40][CH3:41])/[CH:19]=[CH:20]/[C@H:21]1[C@H:28]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[CH2:27][C@H:26]2[C@@H:22]1[CH2:23][C:24](=[O:36])[O:25]2.C(O)(C)C.O>C1(C)C=CC=CC=1>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][C@@H:18]([CH2:37][C:38]#[C:39][CH2:40][CH3:41])/[CH:19]=[CH:20]/[C@@H:21]1[C@@H:22]2[C@@H:26]([O:25][CH:24]([OH:36])[CH2:23]2)[CH2:27][C@H:28]1[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 21225700DiisobutylaluminumhydrideHCID 22827412HCID 22827412, compound

Product 1

HCID 22827413HCID 22827413, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-70 °C

Procedure

17.9 ml of a diisobutylaluminium hydride solution (20% in toluene) are added dropwise, under argon, to a solution of 4.3 g of the lactone prepared in Example (23f) in 84 ml of toluene cooled to -70° C. After 0.5 hour, 1.0 ml of isopropanol and 8.97 ml of water are added to the reaction mixture and the whole is stirred at room temperature for 2.5 hours. The precipitate is filtered off and washed with methylene chloride, and the combined organic phases are dried over magnesium sulphate and concentrated; 4.15 g of the title compound are obtained in the form of an oil.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with methylene chloride
  3. dry with materialthe combined organic phases are dried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-598d80ce44034bddae272e1beb1057d9
Source dataset
uspto-grants-1984_08
Patent number
US04466969

Reaction notes

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