3-Bromo-1-propanol → HCID 11697277, compound

HRID 2261450Notes

Reaction equation

HRID 2261450 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([C:14]2[S:21][C:20]([CH3:22])=[C:19]3[C:15]=2[CH2:16][C@H:17]2[C:23]([CH3:25])([CH3:24])[C@H:18]23)=[O:13])[CH:5]=[C:6]([CH3:9])[C:7]=1[OH:8].Br[CH2:27][CH2:28][CH2:29][OH:30]>C(O)(C)C.[OH-].[Na+]>[OH:30][CH2:29][CH2:28][CH2:27][O:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([CH2:10][CH2:11][C:12]([C:14]2[S:21][C:20]([CH3:22])=[C:19]3[C:15]=2[CH2:16][C@H:17]2[C:23]([CH3:25])([CH3:24])[C@H:18]23)=[O:13])=[CH:5][C:6]=1[CH3:9]

Participants

5

Reactant 2

HCID 123083-Bromo-1-propanolHCID 59593550HCID 59593550, compound2×

Product 1

HCID 11697277HCID 11697277, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-(3,5-dimethyl-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (3.00 g, 8.46 mmol, Intermediate 10) in isopropanol (80 mL) and 2 N aq. NaOH (30 mL) is treated with 3-bromopropanol (2.35 g, 16.9 mmol). The dark red reaction mixture is stirred at 70° C. for 5 h. The solvent is removed under reduced pressure and the residue is dissolved in EA and washed twice with water. The organic layer is dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 1:1 to give 3-[4-(3-hydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-tri methyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (2.55 g) as a yellow oil; LC-MS: tR=1.10 min, [M+1]+=413.33; 1H NMR (CDCl3): δ 6.87 (s, 2H), 3.99-3.90 (m, 4H), 3.04-2.85 (m, 5H), 2.81 (d, J=18.8 Hz, 1H), 2.39 (s, 3H), 2.27 (s, 6H), 2.10-2.01 (m, 2H), 1.93-1.88 (m, 2H), 1.13 (s, 3H), 0.72 (s, 3H).

Workup

  1. customThe dark red reaction mixture
  2. customThe solvent is removed under reduced pressure
  3. dissolutionthe residue is dissolved in EA
  4. washwashed twice with water
  5. dry with materialThe organic layer is dried over MgSO4
  6. customevaporated
  7. customThe crude product is purified by CC on silica gel eluting with heptane:EA 1:1

Sources & evidence

ORD record
ord-ae2c14e1b3514875a4fd7b1aacc553c0
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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