Isopropanol → HCID 87391170, compound

HRID 2261454Notes

Reaction equation

HRID 2261454 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([C:15]2[S:22][C:21]([CH3:23])=[C:20]3[C:16]=2[CH2:17][C@H:18]2[C:24]([CH3:26])([CH3:25])[C@H:19]23)=[O:14])[CH:6]=[C:7](C)[C:8]=1[OH:9])[CH3:2].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl.[CH:32]([OH:35])(C)C>[OH-].[Na+].CC(=O)OCC>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([C:15]2[S:22][C:21]([CH3:23])=[C:20]3[C:16]=2[CH2:17][C@H:18]2[C:24]([CH3:26])([CH3:25])[C@H:19]23)=[O:14])[CH:6]=[C:7]([O:35][CH3:32])[C:8]=1[O:9][CH2:27][CH:29]1[CH2:30][O:31]1)[CH3:2]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 59593545HCID 59593545, compound2×

Product 1

HCID 87391170HCID 87391170, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3-ethyl-4-hydroxy-5-methyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (600 mg, 1.63 mmol, Intermediate 12) in isopropanol (5 mL) and 3 N aq. NaOH (2 mL) is treated with epichlorohydrine (366 mg, 3.95 mmol). The dark red reaction mixture is stirred at rt for 18 h. The mixture is diluted with EA and washed 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 4:1 to give 3-(3-ethyl-5-methoxy-4-oxiranylmethoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (524 mg, mixture of diastereoisomers) as a pale yellow oil; LC-MS: tR=1.18 min, [M+1]+=425.26; 1H NMR (CDCl3): δ 6.89-6.85 (m, 2H), 4.00 (dd, J=2.9, 11.1 Hz, 1H), 3.73 (dd, J=5.9, 11.1 Hz, 1H), 3.48 (s, 2H), 3.37-3.32 (m, 1H), 3.02-2.85 (m, 5H), 2.78 (d, J=18.8 Hz, 1H), 2.64 (q, J=7.6 Hz, 2H), 2.37 (s, 3H), 2.26 8s, 3H), 1.91-1.85 (m, 2H), 1.20 (t, J=7.6 Hz, 3H), 1.11 (s, 3H), 0.70 (s, 3H).

Workup

  1. customThe dark red reaction mixture
  2. washwashed with water
  3. dry with materialThe organic layer is dried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-9ce2ee39735b481cbe1fe2d67eed4029
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

Loading…