Cesium fluoride → HCID 10567448, compound

HRID 1358099Notes

Reaction equation

HRID 1358099 reaction equation
[OH:1][CH2:2][CH:3]=[C:4]([C:6]1[C:7]([OH:20])=[CH:8][C:9]2[C:10]([CH3:19])([CH3:18])[CH2:11][CH2:12][C:13]([CH3:17])([CH3:16])[C:14]=2[CH:15]=1)[CH3:5].[F-].[Cs+].I[CH2:24][CH2:25][CH3:26]>CN(C=O)C.CCOC(C)=O>[OH:1][CH2:2]/[CH:3]=[C:4](\[C:6]1[C:7]([O:20][CH2:24][CH2:25][CH3:26])=[CH:8][C:9]2[C:10]([CH3:19])([CH3:18])[CH2:11][CH2:12][C:13]([CH3:17])([CH3:16])[C:14]=2[CH:15]=1)/[CH3:5]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 336431-IodopropaneHCID 69911148HCID 69911148, compound

Product 1

HCID 10567448HCID 10567448, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2Z)-3-(4-Hydroxy-2-buten-2-yl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-(n-propyloxy)naphthalene (Structure 8 of Schemes 1 and 2, where R1, R4, R6=H, R2 and R3 together form a tetramethyl saturated six-membered carbocyclic ring, R5=methyl, R7=n-propyl). To a flame-dried 25-mL r.b. flask containing 3-(4-hydroxy-2-buten-2-yl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-ol (133 mg, 0.48 mmol) in 2 mL anhydrous DMF at room temperature was added cesium fluoride (365 mg, 2.40 mmol, 5.00 equiv) and 1-iodopropane (52.0 μL, 0.53 mmol, 1.10 equiv), and the mixture was stirred for 12 h. The reaction mixture was then diluted with EtOAc (20 mL) and the resultant organic layer was washed with water (2×10 mL), brine (10 mL), dried (Na2SO4), and concentrated under reduced pressure to afford 150 mg (99%) of (2Z)-3-(4-hydroxy-2-buten-2-yl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-(n-propyloxy) naphthalene as a colorless viscous oil. 1H NMR (400 MHz, CDCl3) 6.91 (s, 1H), 6.77 (s, 1H), 5.78 (dt, 1H, J=6.6, 1.4 Hz), 3.88 (m, 4H), 2.04 (s, 3H), 1.75 (m, 2H), 1.28 and 1.23 (2s, 2×3H), 1.01 (t, 3H, J=7.5 Hz). 13C NMR (100 MHz, CDCl3) 153.3, 144.9, 138.4, 137.0, 127.7, 126.5, 110.1, 70.3, 60.7 35.2, 35.1, 34.4, 33.6, 31.9, 31.8, 25.1, 22.8, 10.7. IR (thin film) 3336 (br, s), 2919 (s), 1498 (m), 1455 (m). Anal. Calcd for C21 H32O2: C, 79.70; H, 10.19. Found: C, 79.60; H, 10.44.

Workup

  1. washthe resultant organic layer was washed with water (2×10 mL), brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b81d16ceed74676991fb005ea6475ff
Source dataset
uspto-grants-2003_07
Patent number
US06593493B1

Reaction notes

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