Iodine → HCID 57212103, compound

HRID 2392946Notes

Reaction equation

[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[CH:14]=[CH:15]\[CH2:16][OH:17])[CH:5]=[CH:4][C:3]1=2.[Zn](CC)[CH2:20]C.II>C(Cl)Cl.ClCl.[Zn]>[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C@H:14]3[CH2:20][C@H:15]3[CH2:16][OH:17])[CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: -22 °C

Procedure

1.67 g of of (Z)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-prop-2-en-1-ol were dissolved in 36 ml of CH2Cl2. At 0° C. 7.62 ml of Et2Zn-solution (1M[hexane]) was added, followed 15 min. later by 1.33 ml of L-(+)-diethyl tartrate, dissolved in 18 ml of CH2 Cl2. Stirring was continued for 45 min. The reaction flask was then cooled to -22° C. and another portion of 13.8 ml of Et2 Zn-solution (1M[hexane]) was added, followed by 2.23 ml of CH2 I2. The reaction flask was allowed to reach +18° C. during 16 h. After quenching with crushed ice/NH4CI-solution, the mixture was extracted with EtOEt, washed with dil. HCI and H2O, dried over Na2SO4 and evaporated to dryness. Flash chromatography (silica gel, hexane/AcOEt=87/13) yielded 1.057 g of (1R,2S)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopropylmethanol, 99% pure according to GC. The absolute configuration was assigned in analogy to Chemistry Letters 1992, 61, but not rigorously proven; the optical purity was determined at the next stage.

Workup

customAt 0° C
waitto reach +18° C. during 16 h
customAfter quenching with crushed ice/NH4CI-solution
extractionthe mixture was extracted with EtOEt
washwashed with dil. HCI and H2O
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-807cd518f95f407c995eb4f3d3c6cf86
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05801253

Reaction notes

Loading…