Acetate → HCID 70631652, compound

HRID 1282883Notes

Reaction equation

HRID 1282883 reaction equation
[OH:1][CH:2]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH:6]1[CH:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15]([O:17]C)=[O:16].C([O-])(=O)C.CO.[OH-].[Na+]>O>[OH:1][CH:2]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH:6]1[CH:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 175AcetateHCID 887MethanolHCID 14798Sodium HydroxideHCID 86733780HCID 86733780, compound

Product 1

HCID 70631652HCID 70631652, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.85 g. of 7-(3-hydroxy-1-octenyl)-1,4-dioxaspiro[4.4]non-6-ylheptanoic acid, methyl ester, acetate in 75 ml. of methanol was treated with 75 ml. of 1N sodium hydroxide and kept at 25° for 0.5 hours. The reaction mixture was diluted with water, washed with ether, acidified with acetic acid and extracted with ether. After washing and drying, the ether extract was evaporated and the residue chromatographed on silica. Elution with 50% ethyl acetate-hexane afforded 0.94 g. of the title product, λmaxfilm 3.0 (shoulder), 3.4, 5.75, 6.85, 8.75, 9.25, 10.4 μ. NMR: 6.35 (S, 2, OH), 5.52 (M, 2, 13 and 14-H), 4.05 (M, 1, 15-H), 3.92 (S, 4, ketal) ppm.

Workup

  1. washwashed with ether
  2. extractionextracted with ether
  3. washAfter washing
  4. customdrying
  5. extractionthe ether extract
  6. customwas evaporated
  7. customthe residue chromatographed on silica
  8. washElution with 50% ethyl acetate-hexane
  9. customafforded 0.94 g

Sources & evidence

ORD record
ord-a912c2e9473a4940932f291cbba3145c
Source dataset
uspto-grants-1976_08
Patent number
US03972917

Reaction notes

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