Acetic Acid → 6-(5-Cholesten-3beta-yloxy)hex-3-yne-1-ol

HRID 128200Notes

Reaction equation

HRID 128200 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][C:31]#[C:32][CH2:33][CH2:34][O:35]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C(O)(=O)C.O>O1CCOCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][C:31]#[C:32][CH2:33][CH2:34][OH:35])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 86737629HCID 86737629, compound

Product 1

HCID 867376286-(5-Cholesten-3beta-yloxy)hex-3-yne-1-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 6-(5-cholesten-3β-yloxy)-1-(triphenylmethyloxy)hex-3-yne (21 g) in p-dioxan (40 ml) is heated on a steam cone until dissolution. This is followed by the addition of 90% acetic acid (30 ml) until turbidity, and the reaction mixture is heated overnight at 100°. Water (15 ml) is added and the mixture is concentrated to a small volume. Ether and petroleum ether are added and crystals (triphenylmethanol) are filtered and discarded. The filtrate is concentrated to dryness and put on a silica gel column and eluted with 20% ether in petroleum ether. The desired compound, 6-(5-cholesten-3β-yloxy)hex-3-yne-1-ol, is isolated as an oil (7.0 g).

Workup

  1. temperatureis heated on a steam cone until dissolution
  2. temperaturethe reaction mixture is heated overnight at 100°
  3. concentrationthe mixture is concentrated to a small volume
  4. additionEther and petroleum ether are added
  5. filtrationcrystals (triphenylmethanol) are filtered
  6. concentrationThe filtrate is concentrated to dryness
  7. washeluted with 20% ether in petroleum ether

Sources & evidence

ORD record
ord-af23b5a353c04835988676bff444e46c
Source dataset
uspto-grants-1981_03
Patent number
US04259324

Reaction notes

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