Acetic Acid → HCID 86733056, compound

HRID 1578666Notes

Reaction equation

HRID 1578666 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][CH2:12][CH:11]1/[CH:22]=[CH:23]/[C:24](=[O:32])[CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[BH4-].[Na+].C(O)(=O)C>CO>[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][CH2:12][CH:11]1/[CH:22]=[CH:23]/[CH:24]([OH:32])[CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86733057HCID 86733057, compound

Product 1

HCID 86733056HCID 86733056, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice cold solution of trans-2-(4-cyclohexyl-3-oxo-1-butenyl)-5-[(tetrahydropyran-2-yl)oxy]cyclopentaneheptanoic acid methyl ester (43 g), prepared in Example 7, in 200 ml of methanol, sodium borohydride (3.8 g) is added portionwise. After stirring for 30 min. acetic acid (4.2 ml) is added. The mixture is concentrated under reduced pressure. The residue is taken up in ether. The ether solution is washed to neutral with water and saturated NaCl solution, dried and evaporated to yield trans-2-(4-cyclohexyl-3-hydroxy-1-butenyl)-5-[(tetrahydropyran-2-yl)oxy]cyclopentaneheptanoic acid methyl ester, νmaxCHCl3 3,450, 1,735, 1,030 cm- 1.

Workup

  1. additionis added
  2. concentrationThe mixture is concentrated under reduced pressure
  3. washThe ether solution is washed to neutral with water and saturated NaCl solution
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-fea8137a9dad4b3eaa9cdbaccd9e4910
Source dataset
uspto-grants-1976_02
Patent number
US03937801

Reaction notes

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