Methanol → HCID 86756381, compound

HRID 634998Notes

Reaction equation

HRID 634998 reaction equation
[CH3:1][C:2]([OH:21])([C:4]#[C:5][CH2:6][C:7]([CH3:20])([CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11]OC1CCCCO1)[CH3:3].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25](S([O-])(=O)=O)=[CH:24][CH:23]=1.[NH+]1[CH:38]=[CH:37]C=CC=1.C[OH:40]>>[OH:40][C@@H:25]1[CH2:26]/[C:27](=[CH:37]/[CH:38]=[CH:11]/[CH2:10][CH2:9][CH2:8][C:7]([CH3:19])([CH3:20])[CH2:6][C:5]#[C:4][C:2]([CH3:1])([OH:21])[CH3:3])/[C:22](=[CH2:32])[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 887MethanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21261643HCID 21261643, compound

Product 1

HCID 86756381HCID 86756381, compound

Procedure

609 mg of 2,6,6-Trimethyl-10-(tetrahydro-pyran-2-yloxy)-dec-3-yn-2-ol (2.05 mmol) was dissolved in 13.5 ml of methanol, treated with 76 mg of pyridinium-(toluene-4-sulfonate) (0.15 eq.), and kept at room temperature for 1 night. The reaction mixture was then poured onto crushed ice/Na2CO3, extracted twice with ethylacetate, washed with brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/ethylacetate=7/3) produced 413 mg of the title compound as yellowish oil.

Workup

  1. waitkept at room temperature for 1 night
  2. additionThe reaction mixture was then poured
  3. extractionextracted twice with ethylacetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d987342508bb47ba870a27470e42af2b
Source dataset
uspto-grants-2001_02
Patent number
US06184422B2

Reaction notes

Loading…