Water → HCID 57167084, compound

HRID 2286077Notes

Reaction equation

HRID 2286077 reaction equation
[CH:1]([CH:3]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH:4]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=O.[C:20]([CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(P(N(C)C)(N(C)C)=O)C>[OH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:4]1[CH:3]([CH:1]=[CH:28][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:27])[CH2:11][CH2:10][C:5]21[O:9][CH2:8][CH2:7][O:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 70073SK&F 45349HCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde

Product 1

HCID 57167084HCID 57167084, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane [4.0 g; prepared as hereinbefore described in Example 1(iv)] and benzoylmethylenetriphenylphosphorane (5.6 g; prepared according to the method of F. Ramirez and S. Dershowitz, J. Org. Chem. 1957, 22, 41) in hexamethylphosphotriamide (35 ml.) was heated on a steam bath under dry nitrogen for 48 hours then poured into water (200 ml.). The mixture was extracted with diethyl ether and the ethereal solution was washed with water, dried over anhydrous magnesium sulphate and evaporated. The residue was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether, allowed to stand at 0° C., then filtered to remove triphenylphosphine oxide. The filtrate was evaporated to give 6-(7-hydroxyheptyl)-7-(3-phenyl-3-oxoprop-1-enyl)-1,4-dioxaspiro[4,4]nonane (5.5 g.) (νmax 950 cm-1, 985 cm-1, 1615 cm-1, 1660 cm-1, 3380 cm-1).

Workup

  1. customprepared
  2. extractionThe mixture was extracted with diethyl ether
  3. washthe ethereal solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether
  7. customto stand at 0° C.
  8. filtrationfiltered
  9. customto remove triphenylphosphine oxide
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-ed58c66cbbf64445a0989081188370f6
Source dataset
uspto-grants-1982_04
Patent number
US04325967

Reaction notes

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