Hexane → HCID 69209576, compound

HRID 902914Notes

Reaction equation

HRID 902914 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:23]([O:25][C:26](=[O:45])[C:27](=[CH2:44])[CH2:28][CH:29]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH3:24].CCCCCC>C1COCC1>[CH2:23]([O:25][C:26](=[O:45])[CH:27]([CH2:44][S:8][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:28][CH:29]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH3:24]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 87734810HCID 87734810, compound

Product 1

HCID 69209576HCID 69209576, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Triphenylmethanethiol (20.58 g, 74.5 mmol) in dry THF (40 mL) was first added drop wise at 0° C. to a suspension of sodium hydride (3.00 g, 74.5 mmol) in dry THF (60 mL). After the addition was complete, the mixture was stirred for 15 min at 0° C. followed by 45 minutes at room temperature. To the resulting suspension, the compound of example 32 (20.58 g, 62.4 mmol) dissolved in dry THF (40 ml) was added drop wise at 0° C. The mixture was then stirred at room temperature until complete consumption of the starting material (2 hours as confirmed by TLC: 97% hexane-3% ethyl acetate). The crude product was isolated as in example 32 and was then purified by flash chromatography (SiO2, 5% hexane-95% ethyl acetate) to afford 28.28 g (75.5% yield) of the desired compound as an oil: 1H NMR (CDCl3, 400 MHz) δ 7.31 (m, 15H), 4.17 (q, 2H), 3.03 (m, 1H), 2.49 (m, 1H), 2.42 (m, 1H), 2.31 (m, 2H), 2.21 (m, 1H), 1.44 (s, 18H), 1.29 (t, 3H); 13C NMR (CDCl3, 400 MHz) 176.3, 167.9, 144.4, 129.4, 127.7, 126.5, 81.5, 66.6, 60.6, 51.4, 42.6, 33.6, 30.4, 27.7, 14.1.

Workup

  1. customwise at 0° C.
  2. additionAfter the addition
  3. waitfollowed by 45 minutes at room temperature
  4. additionwas added drop wise at 0° C
  5. customThe crude product was isolated as in example 32
  6. customwas then purified by flash chromatography (SiO2, 5% hexane-95% ethyl acetate)

Sources & evidence

ORD record
ord-dc591196718340f38be685b468e8b165
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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